Can you believe it’s June? Hard to believe we’re officially halfway through the year.

For a lot of sales teams, this month usually looks something like this: Q2 closes, everyone takes a breath, and Q3 begins anew with many of the same habits you walked out of H1 with. Maybe a few deals have slipped…or pipeline is a little lighter than you’d like…or a rep or two is behind, and you’ve been meaning to address it. But the calendar keeps moving, so you keep moving too. 😪

I get it. Q2 close is exhausting. It feels like you’ve been running a 6-month marathon, and there’s always something more urgent competing for your attention. But, if you’re not careful, that drift is exactly how teams can end up missing the year.

On that bright note 😂, I’d like to introduce the concept of a mid-year audit. This is a structured framework to look at where you actually are, diagnose what’s working and what isn’t, and build a real plan for the back half of the year. Let’s dive in!

📍 A Quick Reality Check

Before we get into the framework, take a quick pause and ask yourself if you can answer these questions without pulling a report…

• Are you pacing ahead of or behind your annual target? By how much?

• Where is your pipeline relative to what you need to close?

• Which reps are at risk of missing the year?

• What’s one thing about your sales process that’s broken and you’ve been tolerating?

If any of those made you uncomfortable...that’s where this series may come in handy. The whole reason you perform a mid-year audit is so those answers stop being surprises. The earlier you find the gaps, the more options you have to close them. If you’ve been reading WRT for a while, you know Christine and I are all about preparation!

🔍 The Audit at a Glance

A mid-year sales audit has two halves - your numbers and your people. We’re starting with the 10,000-foot view this week and will be going deeper on each of these pieces in the weeks ahead.

📊 Half 1: Your Numbers

Pacing to Goal

• Why it matters: At the end of the day, your annual number is the most important number you have as a sales leader. This month’s and this quarter’s forecasts are great yardsticks to measure if you’re on track to hit in the big, but that is all they are. A lot of teams track monthly and quarterly performance without ever stepping back to ask: Are we actually going to hit the year? By June, you should have a good inkling of this, and also have an understanding of why you might be off track (and hopefully what you’re going to do about it in H2).

• Questions to ask:

  • What percentage of your annual target did you close in H1?

  • If H2 has to carry more weight, do you have the pipeline and capacity to support it?

  • Are there any structural changes (new hires, product launches, pricing changes) that should adjust your expectations up or down?

Pipeline Coverage

• Why it matters: A weak pipeline in June is a Q3 (and possibly even a Q4) problem. By the time you feel it, it’s usually too late to fix it for the current year. Coverage tells you whether you have enough opportunity in the system to support your targets, and if you don’t, you need to know now, not in September.

• Questions to ask:

  • What’s your current pipeline coverage ratio for H2 based on current trends?

  • What channels are performing well? What channels need help?

  • Is coverage consistent across reps, or is one person carrying the whole book? Is that planned or not? If not, why is that happening? Is that a lead equity or rep performance issue?

  • Are there any segments or territories where pipeline has dried up? Do you have a contingency plan?

Stage Conversion

• Why it matters: Where deals stall can tell you a lot. I wrote a pretty in-depth article about that here. If opportunities keep piling up at the same stage (demo to proposal, proposal to close, etc.), that’s a signal. It might be a rep skill issue, a process gap, or something your ICP has been trying to tell you. Either way, six months of data is enough to see a pattern.

• Questions to ask:

  • Where in the funnel are deals dying most often? Is this consistent across the team, or are there reps driving this up?

  • Has your conversion rate at any stage changed significantly since January?

  • What are your top three Closed-Lost reasons, and is there a theme? Has that changed over time?

Deal Velocity

• Why it matters: If deals are taking longer to close than they were six months ago, something has changed. Market conditions, your competitive landscape, your team’s execution, or possibly some combination of all three. Slowing velocity is one of the earliest warning signs most leaders miss because it happens so gradually.

• Questions to ask:

  • How does your average sales cycle length today compare to January?

  • Are there deal types or segments where velocity has changed more than others?

  • What’s the oldest open opportunity in your pipeline right now, and what’s the real story there?

🤝🏼 Half 2: Your People

Attainment Distribution

• Why it matters: The team number can hide a lot. One or two strong performers can mask a much bigger problem underneath. A mid-year check on individual attainment tells you who’s carrying more than their share, who’s falling behind, and whether your quota model is still calibrated correctly. This shouldn’t be a surprise if you’re holding weekly pipeline reviews. 😇

• Questions to ask:

  • What does your attainment distribution look like across the team right now?

  • Are the same reps who were behind in Q1 still behind? Or have things shifted?

  • Is anyone sandbagging? (Yes, this is a real audit item because yes, it does happen 👀)

Ramp Status

• Why it matters: If you hired in H1, your ramp timeline matters to your H2 number. A rep who’s behind at month four doesn’t automatically catch up, and a lot of managers wait too long to intervene because they don’t want to lose hope. The audit is your forcing function to look at this honestly.

• Questions to ask:

  • Are your H1 hires on track against their ramp milestones?

  • If someone is behind, is it a skill issue, a pipeline issue, or something else entirely?

  • Do you have enough fully-ramped capacity to hit H2 targets, or are you relying on ramp that hasn’t materialized yet?

  • If you’re planning on hiring in H2, can or will that impact numbers?

Coaching Gaps

• Why it matters: By June, you’ve had enough 1:1s and pipeline reviews to see patterns. Which reps keep getting the same feedback? Where are you as a manager spending most of your time, and is that where you should be spending it?

• Questions to ask:

  • What’s the one skill gap showing up most consistently across your team?

  • Are you spending coaching time where it’ll have the most impact, or defaulting to your strongest reps because it’s easier? Conversely, are you spending way too much time with your “problem children” and ignoring the rest of your team?

  • Is there a rep you’ve been avoiding a hard conversation with?

Process Tolerance

• Why it matters: Every team has something broken that nobody has gotten around to fixing (guilty 😮‍💨). A stage definition everyone interprets differently. A handoff between Sales and CS that keeps causing friction. A discount approval process that takes so long, reps just work around it. You likely know what yours is because you’ve been sweeping it under the rug for the last 6 months (don’t feel bad, we all do it). The back half of the year is harder if you drag it into H2 with you.

• Questions to ask:

  • What’s the one process issue that comes up repeatedly in your team’s complaints or your own frustration?

  • Is this something you can fix in the next 30 days, or does it require a bigger conversation?

  • What’s the cost of continuing to tolerate it for another six months?

🗓️ What We’re Covering This Month

Okay. I know that was a lot. Don’t freak out!

Over the next few weeks, as mentioned, we’ll be going deep on all of the above, along with templates and frameworks you can actually use, not just concepts to think about.

Here’s what that looks like:

• Week 1: Why the mid-year checkpoint matters and the full audit framework at a glance ← You are here! 🗺️

• Week 2: Auditing your numbers - a pipeline and performance diagnostic with a template you can run with your team

• Week 3: Auditing your people - a rep-by-rep assessment framework and a guide for the harder conversations

• Week 4: Building your back-half plan - how to turn everything you found into a clear, prioritized path to December

🚨 Quick note: Weeks 2 through 4 will be subscriber-only. 🚨

If you’ve been on the fence about upgrading, this is a good time to do it. It costs less than a cup of coffee a month! 🙂 You can subscribe here ⬇️

Happy auditing! 🕵🏻‍♀️
Stacy

📚 Stacy’s Book Challenge

This year’s goal is…81. 1 more than last year. 😮‍💨 Follow along as I try to get there.

As of this post, I have read 34 books. Oof - not much progress since last week, though, to my credit I’m reading a 1000-page book lol.

I’m currently reading:

• Dungeon Crawler Carl - Haven’t really touched the book this week 😬

• Blood Meridian - Yeah…no progress here either…I refuse to DNF any book this year, so I’ll try and pick it up soon…

• Gai-Jin - Still having a great time with this one! This has GOT to count for two books 🤣

• Sunrise on the Reaping - Very much in the same vein as all of Suzanne Collins’s other books, so pretty easy read

Follow me on GoodReads! 🤓

In case you missed it, we’ve spent the last few weeks covering:

• 🧽 Days 1-30 (Absorb): Orientation on product, process, and culture before your new rep touches a deal.

• ✈️ Days 31-60 (Practice): How reps can start leading calls while you’re in the room and how to build feedback loops to catch bad habits early.

• 🔑 Days 61-90 (Ownership): What happens when the training wheels are off, and your new AE begins to run their own pipeline.

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All month, we’ve focused on what happens during the ramp. Today, we’re backing up a step and discussing what you should actually have ready before your new AE even shows up. Let’s get into it. 🏃🏻‍♀️

🗺️ A Written ICP

If your new rep doesn’t know who they’re selling to, they’ll figure it out through trial and error, and your customers will be the ones who pay for that education. 🙃 A documented Ideal Customer Profile doesn’t need to be a 20-page deck. A one-pager with clear criteria is enough to get someone aligned before their first call.

What to have ready:

• Firmographic criteria: Company size, industry verticals, tech stack signals, or other defining characteristics of your best-fit accounts

• Persona map: The 2-3 roles most likely to champion your product, what they care about, and how they typically measure success

• Disqualification criteria: A short list of “bad fit” signals so your rep knows what to disqualify early instead of chasing deals that won’t close

• Real-life examples: Pull 3-5 Closed-Won deals that fit the profile and walk through them together in Week 1

💡 Pro-Tip: The disqualification criteria can sometimes be more valuable than the ICP itself. Reps who know what to walk away from early spend more time on deals that can actually close. This helps accomplish two things: they spend time learning from deals that matter and, hopefully, gain confidence chatting with people who can actually buy your product!

🥊 Up-to-Date Competitor Battle Cards

New reps will likely hear competitor names bubble up before they know your product cold. Battle cards give them the confidence to handle those conversations without panicking or winging it. The keyword here is up-to-date. A battle card from two years ago is often worse than no battle card at all, because it gives reps false confidence in positioning that may no longer apply.

What to have ready:

• Battle cards of your top 3-5 competitors: The names your rep will hear most often, in order of frequency

• Where you win: 3-5 clear, honest differentiators per competitor - hint: this should NOT be marketing copy (save that for your website!), but rather, what you and your team have seen actually move deals

• Where you lose: Being honest here builds more trust with your rep than pretending you win everywhere, and actually sets them up for handling objections from real prospects

• Common objections: What prospects say when they’re considering a competitor and the recommended response

• 1-2 competitive deals to sit in on or watch recordings of: Reading about competition is one thing; watching a live competitive deal is another

💡 Pro-Tip: Assign a specific individual on your team (in the early days, it might be you 😅) to own competitive intel. Even a quarterly 30-minute refresh keeps your battle cards far more useful than a doc that lives in a folder that becomes irrelevant over time.

💡 Another Pro-Tip: Your Product team can be an amazing resource here! They often have to do a ton of their own competitive research as they’re building, and can have really interesting perspectives. You’ve heard me say this before - I think the Sales <> CS <> Product trifecta is incredibly powerful when it comes to building balanced messaging that ensures you’re selling the ✨ vision ✨ while also being realistic and practical about what actually sells and keeps the customer around. Use your team!

🔍 A Discovery Framework

Discovery is the foundation of every deal, and it’s also one of the hardest skills to develop without a framework to anchor on. New reps who don’t have one tend to ask surface-level questions, talk too much, or treat the whole conversation like they’re filling out an intake form. None of those builds the kind of trust that moves deals.

What to have ready:

• Core discovery questions: 5-8 questions your rep should be asking in every discovery call, regardless of persona

• Persona-specific questions: How discovery shifts based on who’s in the room (economic buyer vs. end user vs. champion)

• The “why behind the why” framework: Help your rep understand how to connect surface pain to business impact and urgency

• What “good discovery” looks like vs. just checking a box: Give examples of both from real-life deals

• Call review cadence: Plan to debrief on discovery quality, specifically in the first few weeks of co-piloting

💡 Pro-Tip: I’ve found that the best way to teach discovery is typically in the live debrief. After your rep runs their first few discovery calls, sit down and ask: “What did you learn? What would you go back and ask?”

We covered the art (and science) of good discovery earlier this year. This can be a good foundation for what to cover with your rep, especially in the early days.

🤑 Pricing and Discount Guidelines

Pricing conversations happen earlier than new reps expect (sometimes as early as the first call), and when guidelines aren’t documented, margins get negotiated away fast, and/or every rep starts making up their own rules. No bueno. 🙅🏻‍♀️ Your rep should never be put in a position where they have to improvise pricing in a live negotiation.

I wrote a full article on how to build Pricing and Negotiation Guidelines earlier this year, but if you’re just starting out, at a minimum, you should be prepared with the following.

What to have ready:

• Standard pricing (and pricing philosophy): Your rep should know this cold before any customer-facing conversation

• Discount floor and approval thresholds: What can your rep offer on their own, what requires your sign-off, and what goes to Deal Desk or requires leadership approval

• Multi-year and volume pricing: If these exist, document how they work and when it makes sense to introduce them

• Escalation guardrails: A short list of asks your rep should always bring to you before responding

• Real deal examples: Walk through a recent deal where pricing or a pricing-related objection came up and show how you or another rep handled it

  • P.S. Are you noticing a trend here? 👀 The faster your rep can see how your guidelines/rules work in the real world, the more quickly they’ll be able to ramp!

📝 Rules of Engagement

This isn’t necessarily directly deal-related, but ambiguity around account ownership and handoffs is one of the most common sources of friction on early-stage sales teams. Your new rep should never have to guess at what accounts are theirs, how inbound leads get routed, or what happens when there’s a conflict.

I also covered how to build a Rules of Engagement Document earlier this year (we’ve been busy here at WRT!), so feel free to check that out first. If you’re not ready for a fully fledged doc, at a minimum, equip your rep with the following.

What to have ready:

• Territory definition: How accounts are assigned and what determines ownership

• Inbound routing: How inbound leads get distributed and what the expected response time is

• BDR-to-AE handoff criteria: What qualifies a demo or meeting before it gets passed, and who owns it once it does

• Rules around credit and compensation: What are the triggers for reps getting paid and/or for quota relief?

• Conflict resolution process: What happens when two reps both have a claim on an account, and who makes the call

💡 Pro-Tip: Every ambiguous account situation that lands on your desk is a gap in your ROE doc. Start logging them and use them to update your ROE accordingly. Over time, it should become more complete on its own. I know it seems like “a lot” to do early on, but believe me when I say this - mediating territory disputes between reps can be extremely time-consuming for you (and them) and often leads to hurt feelings. Ask me how I know. 😭 Clarity is kindness!

📊 CRM Hygiene Standards

Your pipeline is only as reliable as the data in it, and new reps are one of the fastest ways to introduce bad data if expectations aren’t set up front. Stage labels mean different things in different orgs. Without clear definitions, your rep will fill in the blanks on their own, and you’ll pay for it in forecast accuracy.

If you’ve been here a while, you already know how I feel about CRM hygiene. If not, read about it here so I don’t have to get on my soapbox again. 😂

What to have ready:

• Stage-by-stage definitions: What each stage means at your company, not just what the label says

• Entry (and exit) criteria per stage: The specific activity or proof point required before a deal can advance

• Required CRM fields: What your rep needs to keep updated and why it matters for forecasting and coaching

• Closed-lost hygiene expectations: How quickly deals should be marked, what reason codes to use, and what level of detail you expect in notes

• A walkthrough using a real deal: Reading the stage names in Salesforce is not the same as understanding how your team actually uses them

💡 Pro-Tip: Walk your new rep through a real Closed-Won and a real Closed-Lost deal in your CRM during onboarding. Seeing how a deal actually moved through the stages (and what the notes look like) sets the standard more clearly than any written doc.

💰 A Comp Plan Walk-Through

This one sounds obvious, but you’d be shocked by how many new reps finish their first 30 days without being able to explain how they get paid. Reps who understand their comp plan sell harder, sandbag less, and stay longer. Walking through it in Week 1 takes 30 minutes and can pay off for the entire year.

I am reaalllyyy hoping you already have this before any new AE starts at your org.

And if not, go build this like literally right now. 😂 We wrote some helpful guidelines on how to design sales comp and incentives here.

What to have ready:

• Quota and ramp timeline: What your new rep’s number is, when they start earning variable, and how the ramp guarantee (if applicable) phases out

• Accelerator mechanics: Where they kick in and what overperformance actually pays (I like to use real dollar examples, not just percentages here to make it land more clearly for the AE)

• Deal crediting rules: How multi-year deals, expansions, and co-sells are credited

• Churn and clawback policies: What happens to commission if a deal churns within the first 60-90 days?

• A “what does hitting 100% look like” example: Walk through a full year of attainment so your rep can visualize what success earns them

💡 Pro-Tip: Don’t just hand your AE the comp doc and move on. Walk through it, out loud, with real numbers. In previous roles, I’ve even helped create commission calculators so reps can get a very concrete understanding of what they’re earning (and not just what they’re closing).

🏁 Closing Thoughts

Aaanndd…that’s a wrap on the May ramp series. Thank you for making it this far with me! 🥳 We covered the full 30/60/90 and now the prep work that makes it all possible. The reps who ramp fastest almost always have managers who did the work upfront. The toolkit above doesn’t need to be perfect - it just needs to exist before your new hire starts. Build it once, keep it updated, and every future hire gets a better experience than the last one did.

I’ve got some fun ideas for June cooking in the kitchen now, but please feel free to drop any ideas/requests for content in the comments if there’s anything you’d like to read about first!

Till then, go build some guidelines! ✍️
Stacy

📚 Stacy’s Book Challenge

This year’s goal is…81. 1 more than last year. 😮‍💨 Follow along as I try to get there.

As of this post, I have read 34 books. I finished Everyone on This Train Is a Suspect. Generally a fun book, but tbh there were so many characters and layers of twists that by the end I was like “sure” lol. Fast book to get through, but wouldn’t necessarily recommend it.

I’m currently reading:

• Dungeon Crawler Carl - Continues to not really be my jam 😬 I think I just don’t care for the D&D genre

• Blood Meridian - Yeah…no progress here…

• Gai-Jin - I read Shogun (5 ⭐s for me) and Tai-Pan a few years ago, so now I’m picking up another 1000 pager - this is the 3rd book in Clavell’s Asian Saga series, so good!

• Sunrise on the Reaping - I’m generally not a fan of prequels (somehow they always feel like money grabs after successful series), but figured I’d give this a shot - didn’t realize the movie was coming out later this year, so that’ll be a fun accompaniment!

Follow me on GoodReads! 🤓

If you’re just joining us, here’s a quick recap of where we’ve been:

• In Week 1, we covered your new rep’s first 30 days, which are all about absorbing product knowledge, process orientation, shadowing calls, and understanding your team and sales culture.

• In Week 2, we talked about Days 31-60, where your rep starts leading deals with you in the room as co-pilot. The emphasis is on building real feedback loops, running structured debriefs, and coaching in the moment without taking over.

This week, we’re crossing into the final stretch of the 30/60/90, where we’ll cover how your new rep starts taking real ownership of their deals and pipeline. Let’s get to it! 🏁

🔑 Days 61–90: Ownership

Let’s start with what ownership actually means, because finding the right balance can be tricky. On one end, you let new reps run every call on their own (and risk them falling flat on their faces). On the other, you jump in to rescue them every time a prospect asks a tough question. As you can probably imagine, the right answer lies somewhere in the middle of that spectrum.

By Day 90, you’re still present as a coach - you’re just no longer co-piloting. That distinction matters because many managers never fully make the shift. They stay in co-pilot mode too long, jumping on every call, rewriting every email, and answering questions the rep should be solving themselves.

While it may feel like you’re protecting deals (or your reps) from failing, you may actually be delaying development. The rep never builds the confidence that comes from truly owning the job, and you never get a clear picture of what they’re capable of on their own.

🧭 What Ownership Actually Looks Like

By Day 90, your rep should be able to do the following without significant hand-holding:

• Run a full sales cycle fairly independently, from discovery through close. They know the motion and what your expectations are at each stage, they know the questions to ask, and they know when and how to escalate. They’re not perfect, but they’re not lost either.

• Self-identify where they need help. A rep who can say, “This deal is stuck and here’s why I think that is. Can you help me?” is significantly more developed than one who waits for you to spot it during pipeline reviews. Coaching toward that instinct is one of the most valuable things you can do in this phase.

• Manage their own follow-up. You shouldn’t have to ask, “Did you follow up with that account from last week?” They’re already doing it (and hopefully logging it in the CRM 🙏🙏🙏). They’re not waiting on you to remind them to perform basic tasks.

• Walk you through the basics of their pipeline without prompting. They know their data, such as estimated deal sizes and close dates, and can give you insights into which deals are generally healthy and which need help (and what they think might be the reason).

None of this means the AE is operating in a vacuum. You should already be running regular 1:1s with them, reviewing their pipeline together, and helping them with consistent deal strategy sessions. The difference is that they’re bringing the agenda, coming in with their own ideas and asks, and sharing their own hypotheses about what needs to happen next. (p.s. I wrote an article about what it looks like when an AE evolves from simply knowing their book of business to owning it, and later, being able to drive it! 🏎️💨)

🎯 What to Focus On as a Manager

Your job in this phase is threefold: develop judgment, build pipeline discipline, and set up the Day 90 conversation.

Develop judgment, not just process.

In the first 60 days, you were teaching the rep how things work. In Days 61-90, you’re teaching them how to think. That means asking more and telling less in your pipeline reviews. Evolve your conversations:

• “Here’s what I’m seeing.” ➡️ “What’s your read on where this deal is?”

• “Here’s what you need to do.” ➡️ “What do you think you should do next?”

• “Here’s how I’d handle that objection.” ➡️ “How would you respond if they push back on pricing?”

You’re building a rep who can figure things out, not one who always needs the answer handed to them.

💡 Pro-Tip: One specific thing worth coaching is how reps should handle not knowing something on a call. New reps often freeze or overpromise in moments of uncertainty. No bueno. 🙅🏻‍♀️ Good ones learn to say “let me confirm that and follow up with you by Friday” and then actually do it. That’s a habit you can reinforce consistently in debriefs.

Build pipeline discipline early.

Day 61 is a great time to set the expectation that pipeline ownership is not optional. A rep should never walk into a pipeline review or a 1:1 without knowing their numbers cold. If you’ve been running structured pipeline reviews as a team, your new AE should already be seeing what that looks like in practice. Now they’re expected to participate the same way everyone else does.

This is also the window to reinforce CRM hygiene as a habit, not a chore. I get on my soapbox about this every few weeks, so you’ve probably heard me say this 1000 times already. 😂 The reps who stay on top of their CRM are the ones who can actually manage their book of business. The ones who treat it as an afterthought tend to lose track of things that cost them deals later. Friendly but consistent reminders now prevent hard conversations later.

Similar to the above, conversations should grow with your rep. This can look like:

• “Do you have an update for this deal?” ➡️ “Walk me through your pipeline for the month.”

• “Your forecast looks light.” ➡️ “Which deals are you most confident in, and why?”

• “You missed updating this opportunity.” ➡️ “What’s your process for keeping your pipeline current?”

Set up the Day 90 conversation early.

Quick tip - don’t let Day 90 sneak up on either of you. Around Day 75, start signaling that the 90-day check-in is coming and what it’s going to cover. You’re not trying to create anxiety. You’re giving the rep a fair runway to know what they’re being evaluated on and to finish the ramp strong.

📋 The Day 90 Check-In

So what should the Day 90 conversation look like anyway? In my opinion, this is one of the most important conversations you’ll have with a new AE, and unfortunately, it’s also the one most managers handle the least intentionally. I mentioned this in an earlier article, but the more you take your reps seriously, the more they’ll take you seriously. Show them (even the newbies) the respect that they deserve!

A few things I’d recommend covering:

• Review the 30/60/90 together. Go back to the doc you built before they started. Where did they land relative to each milestone? Be honest and specific. This conversation is most useful when it’s grounded in actual performance.

• What’s working and what isn’t. Hint: This should go both ways. You should share your observations with your rep, but invite them to share theirs as well. Good reps at Day 90 will often have real, useful feedback about the onboarding process, the tooling, or the support they did or didn’t get. That’s worth listening to! Develop a plan if there are specific gaps you (or they) want to shore up.

• What comes next. Day 90 is not the finish line - it’s simply a milestone. Use this conversation to set clear expectations for the next 90 days. What does full ramp look like? What are you watching for? What does success in the next 1-2 quarters actually require of them?

💡 Pro-Tip: Resist the urge to make the Day 90 check-in feel like a performance review. While there is an expectation of ownership, keep in mind that they are still really new. Research shows that most new employees don’t actually feel like they have their feet under them until at least 6 months in. You want the rep to leave that conversation feeling clear on where they stand and motivated to close the gaps, not completely freaked out.

⚠️ When a Rep Is Behind at Day 90

This is a way less fun topic, but I think it’s important to have contingency plans. Sometimes you get to Day 90, and the rep isn’t where they need to be. The mistake a lot of managers make here is softening the message so much that the rep doesn’t actually hear it. I see this happen because it often takes a long time to get the right person in seat, and the last thing you want is to lose them for any reason.

If a rep is behind at 90 days, I’d recommend a few things:

• Be direct but not punitive. Name the gaps clearly and tie them to observable behavior, not personality. “Your CRM is consistently behind, and it’s costing you visibility into your pipeline” is more actionable than “I don’t think you’re taking this seriously”.

• Build a clear improvement plan with a timeline. What needs to change? By when? What does success look like at Day 120? Day 150? Put it in writing. This protects both of you and gives the rep a roadmap instead of just a warning.

• Don’t wait until Day 90 to have this conversation. If you’re doing your job in Days 61-75 (and honestly before), you shouldn’t have any surprises at the 90-day mark. The check-in should confirm what you’ve already been working on together, not deliver news that blindsides them.

The managers who dread this conversation the most are usually the ones who haven’t been giving real feedback throughout the ramp. If you’ve been specific and consistent from Day 1, Day 90 is usually just a recap of things the rep already knew.

✅ A Quick Checkpoint Framework

Summarized, here’s a simplified version of what I look at when assessing where a rep is at Day 90:

• Do they know their numbers without being asked?

• Are they running routine calls independently and debriefing themselves?

  • Do they know who to escalate to and how to ask for help for difficult calls?

• Is their pipeline real? Is it properly staged, up to date, and grounded in actual next steps?

• Can they articulate why deals are moving or stalling?

• Are they coming to 1:1s with their own agenda and/or their own asks?

• Have they closed at least one deal, or do they have a clear path to one in the near term?

  • Quick note: Depending on your sales cycle, you may or may not expect a close within the first 90 days. Make sure the rep knows what’s realistic and what the bar is before they hit Day 90, not the day of. Also, make sure you’re setting them up to succeed - if it’s reasonable for them to close a deal by Day 90, make sure you’re also helping to set them up with pipeline coverage that will allow them to make that possible.

📦 Closing Thoughts

We’ve spent three weeks walking through the 30/60/90 from a manager’s perspective. Next week, we’re closing out May with something a little different: a full toolkit for new AEs. Everything a rep needs to hit the ground running, from the questions to ask in the first week to the habits that separate the ones who ramp fast from the ones who flounder. Whether you’re a manager who wants to hand your new hire something useful or a new AE trying to figure out how to approach this, next week’s article is for you.

There’s also going to be a bonus article covering how to ramp experienced AEs as well as BDRs, so stay tuned. 👀

Till then, finish out that ramp strong! 📈
Stacy

📚 Stacy’s Book Challenge

This year’s goal is…81. 1 more than last year. 😮‍💨 Follow along as I try to get there.

As of this post, I have read 33 books. I ended up finishing The Wager - I’ve been reading books that are way out of my usual fare this year, and that’s been pretty fun. It’s a pretty interesting story about a shipwreck in the 1700s and how its crew did (or didn’t make it). Pretty insane stuff!

I’m currently reading:

• Dungeon Crawler Carl - Okay I know this is suuuper popular with folks…I’ll be honest, it’s just not really my cup of tea 😬

• Blood Meridian - Not a big fan of this one either…this is going to take me a while

• Everyone on This Train Is a Suspect - One of those pop murder mysteries…I usually like them as light fare, but this one’s just been so-so for me so far

Follow me on GoodReads! 🤓

Welcome back to May’s AE ramp series! Last week, we covered the first 30 days of getting your new AE up to speed, discussing how to get them oriented, introduced to the product, plugged into the team, and through their first shadowed live call. The goal is simple: don’t let them walk into Month 2 confused about who you sell to, what you sell, or how your team operates.

This week, we’re moving on to days 31 through 60 of your AE’s ramp. This is where they get the opportunity to put all the great information you’ve given them into practice.

Let’s get into it! 🏃🏻‍♀️

✈️ Days 31-60: Practice

At around the 30-day mark, the training wheels aren’t fully off yet, but your AE should no longer just be watching. They’re beginning to dip their toes in actual deals. For managers, the temptation can be very strong to either hover too much (taking the call over the moment it gets awkward) or disappear too much (handing them the keys and hoping for the best). As you can imagine, neither is ideal. Days 31 through 60 are for co-piloting, and that means you actually show up as a coach, not a player or a spectator.

As reps begin to own deals, they should begin to be responsible for running calls, but with backup in the room (literally or digitally). Having backup matters for one very important reason: you typically train new hires on the “happy path” because it usually has the most generalizable outcome. Most new reps have an idea of what to do if the prospect shows up curious, asks good questions, and moves forward. If only that happened every time.

Alas, real deals don’t usually go that way. Prospects have an insane knack for asking the most off-the-wall questions, and having a manager or peer in the room for those moments is a really efficient way for new reps to learn how to handle objections and surprises in real time, with real stakes, without completely derailing a deal they’ve been working.

💡 Pro-Tip: I’m a big fan of mixing up co-pilots on deals - sometimes it should be you as the manager, and sometimes it’s a tenured peer. Seeing different people sell the same product is one of the fastest ways a new rep can develop their own style and also get exposure to a bunch of different ways to answer prospects’ questions.

Targeted coaching should also be happening throughout this entire phase, not just at the end. The difference is calibration:

• Days ~31-45: Be generous. These are your AE’s first real shots on goal. They’re going to mess things up. Lord knows I still do, and I’ve been selling for a LONG time. 🫠 Your job is to help them debrief, identify what happened, and let them try again.

• Days ~46-60: Start holding the line on things you’ve already flagged. If they’re repeating the same mistake after you’ve addressed it two or three times, that’s the conversation to lean into. Ongoing patterns need direct feedback.

The goal of this phase isn’t to close deals, especially if your typical cycle time is more than 30 days. If they’re able to get deals done, amazing - let me know so I can hire them lol. But really, the goal is for them to develop consistent habits on every call and build real confidence by the end of the month. Those two things will matter a lot more in Month 3 when quotas typically start to count.

🎙️ The Feedback Loop

The most important thing you can do in this phase is to build a real feedback loop that is structured, consistent, and specific.

Here’s the cadence I’d recommend:

• Right after the call: Quick debrief, even if it’s just 10 minutes. What went well? What would they do differently? Ask them first before you give your take. You’ll learn a lot about their self-awareness, and it keeps the conversation collaborative instead of prescriptive.

• Weekly 1:1: Review a call recording together. This isn’t an exercise for you to nitpick every word, but rather where you can help to identify one or two things worth working on. Specificity matters here. “Your discovery questions were good” is nice, but not useful. “When they mentioned their ops team was overwhelmed, you moved on instead of digging in. That was the moment to push deeper,” is something they can actually act on.

• End of phase check-in: Around Days 55-60, complete a more formal review. Where have they grown since Day 30? Where are they still getting stuck? This should map back to whatever 30/60/90 milestones you set on Day 1.

💡 Pro-Tip: If you’re using a call recording tool like Gong or Chorus, encourage your reps to listen to their own calls and call out things they thought they did well or what they could improve on. Do the same for them. Think of it like watching game tape - the best teams have dedicated time set aside to review their own plays so they know how to improve for the next game.

💡 Another Pro-Tip: If you have a Sales Engineering team that supports your AEs on calls, they can also be an amazing resource for feedback, directly to the AE and also to you. We have an amazing relationship with our SE team at SupplyPike, so reps are getting input from a bunch of different angles!

📋 CRM Discipline Starts Now

One thing I see managers overlook quite a bit in this phase is CRM hygiene. A rep who doesn’t update the CRM in Month 2 won’t suddenly start doing so in Month 6. 😮‍💨 I wax poetic about why keeping a clean CRM is important, and I want to reiterate that here. Not only will it save you a ton of heartache when you’re working on reporting later, but a rep who knows how to keep clean records from the beginning is a rep you can actually coach, forecast with, and cover for when they’re out of office.

A few things to set expectations on now:

• What does a “complete” deal record look like in your CRM? Define it. Don’t assume they know.

• When should they be updating deal stages? (After every call? Same day? End of week?)

• Where do call notes live, and how detailed should they be?

• What’s the trigger to move a deal forward to the next stage?

If you’ve already built out a pipeline review process (we covered this a few months ago), now is also a great time to start looping your new AE in as an observer for their peers. Let them see how you think about stage discipline and deal health, and how fellow AEs are expected to report on their book of business, before they’re fully on the hook for it themselves.

🚨 What to Watch Out For

A few patterns I’ve seen derail reps in this phase…

👂 Happy Ears

• What this is:

  • One great call and suddenly the deal “feels like it’s going to close”.

• Signs:

  • Deal stages that are advancing too fast with no corresponding activity

  • Vague answers when you ask about next steps

  • CRM notes that say “good call!” and nothing else

• How to correct:

  • Pull up the deal together and walk through the evidence. What did the prospect actually say? What does “done” look like on their end? Teach them to separate positive signals from buying intent. Confidence is great…complacency will cost them later.

🐣 The Baby Bird

• What this is:

  • The rep who keeps asking to shadow more calls before going solo, or who routes every prospect question back to you instead of handling it themselves.

• Signs:

  • Still deferring to you mid-call by Day 45

  • Asking “can you just take this one?” more than once

  • Avoiding scheduling their own calls or sending emails without prompting

  • Overdependency on sales engineers or product managers (of course, they’re there to help with the sale, but your AE should still be responsible for quarterbacking the call)

• How to correct:

  • Name it directly, but with empathy. “I’ve noticed you’re still pulling me in for things I think you’re ready to handle. Let’s talk about that.” Then put them in low-stakes situations intentionally so they can build evidence that they can do it.

😬 The “I Already Know How to Sell” Rep

• What this is:

  • Usually your most experienced hire. Five years of sales, great instincts, and a quiet (or not so quiet) assumption that the co-pilot phase doesn’t really apply to them.

• Signs:

  • Pushback on shadowing or feedback

  • Skipping debrief notes

  • Adapting your sales motion to their old one and ignoring your process

• How to correct:

  • Set the expectation on Day 1 that everyone goes through this phase the same way. Frame it as “learning how we specifically sell” rather than “learning how to sell”. Their experience is an asset, and it’s important not to baby them. That said, everyone has things they can improve on, and reps that assume they don’t need coaching can be very dangerous for your culture in the long run.

🤐 The Feedback-Shy Manager

• What this is:

  • The manager who softens feedback so much in the early weeks that the rep doesn’t actually know what they need to fix.

• Signs:

  • Debriefs that feel like pep talks

  • Feedback that’s all “here’s what you did well” with nothing actionable

  • Avoiding a hard conversation because they’re “still getting their footing”

• How to correct:

  • Remember that gentle course corrections in Month 2 are a gift. The same conversation at Month 5 is a lot harder for everyone. You can be kind and specific at the same time.

📖 If You’re a Rep Reading This

A few things to keep in mind from the other side of the table:

• Be genuinely coachable. Don’t just nod along in the debrief and then keep doing the same things. If you’re getting feedback on something specific, try changing it in your very next call and tell your manager you did. And if you disagree or feel unclear about your manager’s feedback, have a conversation! It helps no one if you agree out loud, but then make no changes or feel resentful about the coaching you receive.

• Own your pipeline, even if it’s tiny. You may only have two or three active deals right now, and that’s fine. Treat them like they’re your whole quarter. Build the habit of knowing every deal cold, having a clear next step on all of them, and updating the CRM as if someone will be auditing it. (Spoiler: they likely will.)

• Ask for call reviews. Don’t wait for your manager to pull a recording - send one you’d like coaching on. Go back and listen to your own calls. You’ll catch things you didn’t notice in the moment. Pick one thing to fix on the next call. Rinse and repeat.

  • If you have tenured peers, ask them to share their favorite calls with you, or if you can shadow one of their deals. Learn vicariously from the best.

• The goal isn’t to close right now. Your job in this phase is to develop. Close what you can, but don’t let pressure to hit a number make you rush deals or skip steps. A rushed deal that falls apart hurts everyone more than a clean loss does.

🏁 Closing Thoughts

By the end of this phase, here’s what a rep on track looks like:

• Running calls independently (but not perfectly) with confidence

• Showing coachability where you can see them applying feedback across calls

• Keeping up CRM hygiene without being reminded

• Starting to build a small but real pipeline

• Knowing their own strengths and gaps (not just when you tell them, but when you ask them)

  • This is a big one. Reps who can accurately self-assess are the ones who grow fast. If they can tell you, “I’m pretty good at discovery, but I lose momentum in the trial,” you have a real coaching partner. If they think every call went great, you’ve got more work to do.

Next week, we’re moving on to days 61-90: the Ownership phase. This is where the real proving grounds begin. Quota expectations usually start around this time, and the reps who built strong habits in the first 60 days start pulling ahead fast. See you there!

Till then, happy co-piloting! 👩🏻‍✈️
Stacy

📚 Stacy’s Book Challenge

This year’s goal is…81. 1 more than last year. 😮‍💨 Follow along as I try to get there.

As of this post, I have read 32 books. Back to real life, unfortunately. I finished Pachinko, and just started watching the Apple+ series. The book had a really solid first two-thirds, but kinda fell apart in the end for me. Still a solid read though!

I’m currently reading:

• Dungeon Crawler Carl - Pretty fun read so far, leans a little YA

• Blood Meridian - Won’t lie…not a fan of this one…

• The Wager - Recommended to me by a friend! If you recall, I read Pirate Latitudes last month…this is basically that but in real life lol

Follow me on GoodReads! 🤓

I took a short break from writing after coming back from Paris, where we ate entirely too many croissants, napped in the Luxembourg Gardens, strolled along the Seine every day, and visited every landmark you can think of. 😌

It was amazing! That said, I’m back and ready to chat all things sales. 🤑

Last month, we wrapped up our discussion on deal execution from the rep’s perspective, covering discovery, demos, objections, and closing. This month, we’re shifting gears to something I get asked about a lot: how do you actually ramp a new AE?

We’ll walk through the first 30, 60, and 90 days, then close the month out with a toolkit of everything a new rep needs to get started. If you’re a leader who just made a hire, a manager inheriting a team, or a new rep yourself trying to figure out what the first few months should look like, this is for you!

🧭 Start Here: The 30/60/90

Before we get into the week-by-week stuff, I want to zoom out and talk about the document that ties the whole thing together: the 30/60/90 plan. It’s a little old school, but I’m a big fan. When done correctly, you set expectations for your reps with clear milestones, defined focus areas for each phase, and a shared understanding of what success looks like at each checkpoint.

Here’s the simple framework I like to use:

• Days 1-30: Absorb. The rep’s job is to learn, observe, and get oriented.

• Days 31-60: Practice. They really start dipping their toes in selling, with coaching and feedback built in.

• Days 61-90: Own. They begin leading the process. You start coaching, and stop carrying.

We’ll cover the 31-60 and 61-90 windows over the next two weeks. But everything downstream depends on getting the first 30 days right, so let’s start there.

🧽 Days 1-30: Absorb

The first 30 days are about input, not output.

The most common mistake I see managers make is putting a new rep in front of a prospect before they actually know what they’re selling, who they’re selling to, or how the team operates. When the rep gets dedicated time to learn, almost everything else gets better.

Here’s how I would break it down, week by week.

📅 Week 1: Orient

🎯 Purpose:

Get the new hire settled and the manager-rep relationship started on the right foot.

📖 Context:

Week one sets the tone for everything that follows. New hires are absorbing a lot at once - your company, your product, your culture, and your team dynamics. They’re also trying to figure out how much they can trust their manager and whether the job is what they thought it was going to be. This is your chance to make a strong first impression as a leader.

✅ What To Do:

• Block time on day one (or day two at the latest) for a real sit-down. Walk through the 30/60/90 and their comp plan together, share your expectations, and cover how the team operates.

• Get recurring 1:1s and pipeline reviews on the calendar before the week is over.

• Make sure they have access to everything they need: your CRM, call recording tool, metrics dashboard, and internal wiki. This should be staged and ready before they arrive. (Check out Christine’s article on Resource Management here!)

• Get them plugged into the right channels on Slack (if available), like the AE team channel, any channels that show Closed-Won or Closed-Lost deals (genuinely one of the best learning resources available), and wherever your team goes for deal support (like a Deal Desk).

• Start them on your product training or onboarding curriculum. If you’re early in the game, even a curated list of call recordings (more on this later) and docs can be a great place to start.

🚫 What To Avoid:

• Dropping a Slack message with 15 links and calling it onboarding. 🙅🏻‍♀️

• Skipping the 30/60/90 walkthrough. Handing someone the doc without discussing it is almost as bad as not having one.

• Letting tool access requests drag into week two. Nothing kills momentum like a new hire spending their first week chasing down logins.

  • Christine and I are pretty relentless in our belief in minimizing your employees’ TTV. 😤

📚 Good Resources To Share:

• Their 30/60/90 plan

• Their goals and comp plan

• Your company’s orientation deck (Christine covers a lot of great content on this here!)

• Product documentation and onboarding curriculum

• Links to your most important internal Slack channels

• CRM, call recording tool, and metrics dashboard access

📅 Week 2: Learn the Process

🎯 Purpose:

Help the new hire understand how your sales motion actually works from the people living it, not just from a slide deck.

📖 Context:

There’s a big difference between knowing that your company sells something and understanding how deals actually move. Week two is about closing that gap. Cross-functional relationships and early exposure to call recordings are the two fastest ways to build real context before they ever talk to a live prospect.

✅ What To Do:

• Schedule 30-minute cross-functional coffee chats between the new rep and the key people they’ll work with: whoever owns sales collateral, the business case process, customer operations, integrations, etc. The goal is to help them understand how each role connects to the sales cycle and who to call when things get messy.

• Give them a prompt for these chats. It can be something as simple as: how does your role touch the sales process, what does a good handoff look like, and what do you wish AEs understood better? That last one always gets the most useful answers. 😪

• Start watching call recordings. A minimum of three to start: one early-stage demo or intro call, one mid-stage business case or presentation, one late-stage contract or negotiation. This gives them a feel for the full arc before they dive into more Product knowledge and sit in on a live call.

• Debrief after the recordings. What did they notice? What surprised them? What questions came up? Don’t just send the links and move on.

🚫 What To Avoid:

• Making the cross-functional chats optional. New reps who skip these almost always regret it later when they’re scrambling to figure out who to call mid-deal.

• Skipping the call recording debrief. The debrief is where most of the learning actually happens.

• Overwhelming them with too many recordings at once. Three well-chosen calls with context are better than giving them a login to Gong and saying “good luck”.

📚 Good Resources To Share:

• A curated list of call recordings across each deal stage (demo, business case, negotiation)

• Your sales deck and any core collateral

• Your business case template or process doc

• A list of cross-functional contacts and what they own

📅 Week 3: Understand the Role

🎯 Purpose:

Go deeper on the actual craft of the role - cover things like deal flow, methodology, key metrics, and common scenarios they’ll face.

📖 Context:

By week three, the new hire has context but not conviction. They’ve seen how things work from the outside. Now they need to understand the “why” behind the process, what “good” looks like at each stage, and what guardrails exist. This week is about turning observation into understanding.

✅ What To Do:

• Start shadowing live calls as a silent observer. There’s a huge amount to absorb from observation alone, and reps who skip this step almost always develop habits they have to unlearn later.

  • I love this step even for folks coming in with sales experience. All sales teams do things differently and with different terminology. Make sure they’re aligned with yours (and see what you can learn from them!).

• Schedule peer sessions with other AEs to cover: typical deal flow from lead to close, your discovery and demo methodology, key metrics and activity expectations, the top objections they’ll hear and how the team handles them, and negotiation guardrails (what they can do, what needs escalation, who to loop in).

• Set up coffee chats with the product team. Similar to the cross-functional chats in week two, the goal here is to make sure the new rep feels comfortable talking about your product with confidence. Have them spend 20-30 minutes with whoever owns each core product area. They don’t need to come out of these calls as a product expert. They just need to know enough to speak to it naturally and know who to loop in when the questions get technical.

• If your team has access to external sales training resources like on-demand courses, recorded workshops, etc., now is a great time to start layering those in alongside the internal shadowing. Reps tend to make connections faster when both are happening at the same time.

• Keep watching recorded calls. By the end of week three, I’d expect a new rep to have watched six to eight calls across all stages.

🚫 What To Avoid:

• Letting them participate on live calls before they’re ready.

• Assuming they’ll figure out your methodology by osmosis. If you have a defined process, share it explicitly.

• Skipping the metrics conversation. Reps who don’t know what “good” looks like can’t self-assess, and that makes coaching a lot harder.

📚 Good Resources To Share:

• Your discovery and demo framework or methodology doc

• Key metrics and activity benchmarks for the role

• Your top objections doc or battle cards

• Negotiation guardrails and escalation paths (I provided a step-by-step on how to build that here)

• ROEs between teams (another step-by-step for this is here)

• Any external sales training resources your team uses

📅 Week 4: Build Confidence

🎯 Purpose:

Get the new rep selling for the first time, with support in place.

📖 Context:

Week four is where the foundation gets tested. The new hire has absorbed a lot, and now it’s time to see how it holds up in practice. To be clear, the goal isn’t a polished performance. This is simply a first rep, followed by honest feedback, followed by a couple of things to work on.

✅ What To Do:

• Run a bunch of mock calls first. Have a teammate or manager play the prospect and walk through a realistic scenario, including intro, discovery questions, a demo, and maybe a curveball objection or two.

• Debrief the mock immediately. Same rules as a live call debrief: ask them how they thought it went first, then give specific, honest feedback. What worked, what didn’t, and what to tighten up.

• Once they’ve done the mock and had the debrief, do it again. And again. And again. Until you feel good about having them lead a call.

  • 💡Pro-Tip: Depending on how established your Sales Enablement team is, you can even work with them to create tests/certifications that your new reps (or even seasoned ones) have to pass before they can start selling.

• Then, have them lead one live call with a teammate or manager present to have their back if things go sideways.

• Debrief the live call too. Don’t skip this one just because the mock already happened. The live debrief is a different conversation and usually surfaces different learnings.

🚫 What To Avoid:

• Skipping the mock calls and going straight to live. I’m getting nervous just thinking about it lol.

  

  • I know it feels a little awkward to roleplay. Do it anyway. Finding the gaps in a safe environment is way better than finding them mid-demo with a real prospect.

• Keeping debrief feedback generic. “Good job!” or “You could have done that better” doesn’t help anyone. Get specific.

• Adding quota pressure before the 30 days are up. If the 30/60/90 says this is the absorb phase, hold the line on that. I talk about building a ramp period into your comp plans here.

  • 💡 Pro-Tip: Make sure you have alignment on ramp time with your ELT as well. The last thing you want is for your CEO to be breathing down your neck, asking why your new rep hasn’t closed any deals when it’s, like, day 10. 🙃

📚 Good Resources To Share:

• Product one-pagers and positioning docs for each core product area

• Common questions and how to handle them (a simple FAQ doc goes a long way)

• Your pricing and packaging overview

By the end of day 30, here’s what you should be looking for from your reps:

• They can talk about your pain points and your product reasonably comfortably

• They’ve watched the full deal cycle multiple times and can walk through each stage

• They have real relationships with the cross-functional and product people they’ll work with

• They’ve led at least one call with support

• They know their key metrics and understand what “good” looks like for their role

• They know who to go to if they have questions about any of the above

📝 A Note for Managers

The first 30 days are as much a test of the manager as they are of the new rep.

I’ve seen really thoughtful onboarding plans completely fall apart because the manager handed off the doc and disappeared into their calendar. You built the structure - now you have to actually show up for it. Be in your 1:1s. Debrief after their first live call. Answer questions the same day, not three days later.

New hires are paying close attention to everything in those first few weeks. They’re figuring out how much they can trust you, whether it’s actually safe to ask dumb questions, and whether the culture you described in the interview is real. The first 30 days are your chance to show them it is!

And please, I mentioned above, but I’ll say it again. Don’t add pressure that wasn’t in the 30/60/90. If you told them the first 30 days are about absorbing, don’t start asking about pipeline in week three. It creates anxiety that gets in the way of actual learning. The revenue will come. Let them build the foundation first.

📈 Closing Thoughts

Good ramp programs don’t have to be complicated! They do have to be intentional. The difference between a rep who hits their stride at month three and one who’s still struggling at month six is almost always traceable back to what happened (or didn’t happen) in the first 30 days.

Next week, we’re moving into days 31-60: the Practice window, when reps start leading calls, getting real feedback, and building real momentum. It’s also where a lot of ramps start to go sideways without the right structure in place. We’ll talk about what to do and what to watch for. 👀 I’ll also be writing a bonus article on how to adapt this for ramping BDRs.

Till then, happy ramping! 🛹
Stacy

📚 Stacy’s Book Challenge

This year’s goal is…81. 1 more than last year. 😮‍💨 Follow along as I try to get there.

As of this post, I have read 31 books. Made a TON of progress in Paris, as you can imagine. 💁🏻‍♀️ I finished…

• All Quiet on the Western Front - another 5 ⭐️ for me!

• Real Americans - really strong writing, but I feel like it kinda fell apart in the last 25%

• Slaughterhouse Five - I’m so sorry, I just thought it was fine…please don’t come at me 😫)

• The Sword of Shannara - I finally finished it lol

• The South - set in Malaysia, which I was excited about, but…it was fine - reminded me a lot of Call Me By Your Name

I’m currently reading:

• Pachinko - Finally getting back to this!

• Dungeon Crawler Carl - And this!

• Blood Meridian - This one is just gruesome, but everyone recommended it after No Country for Old Men…so here I am lol

Follow me on GoodReads! 🤓

As Christine mentioned, we’re bringing this week’s edition of Weekly Roundtable to you all the way from Paris. I’ve had a croissant, a pain au chocolat, a crêpe, and a couple of macarons in just 1.5 days, so we are off to a GREAT start. 😂

If you’ve been following along, we’ve made it to Week 4 of our deal execution series. This month, we’ve covered discovery, running demos that sell, and navigating objections and stalled deals. Today, we’re wrapping it all up and putting a bow on it by talking about closing strong and handing off the deal.

Let’s dive in! 🐬

🏁 Part 1: Driving It Home

📬 Engagement Is Your Best Signal

It may seem counterintuitive, but the volume of communication with a prospect tends to increase when a deal is getting close. When they’re asking questions about implementation, billing, or what onboarding looks like, you’re usually in a pretty decent spot. Active engagement means your prospect is already mentally bought in and is figuring out what it’ll take to implement your product. Ensure you’re matching their energy, answer their questions thoroughly, and keep the momentum alive.

If a prospect goes quiet late in the cycle, that’s the real red flag. 🚩 Don’t just wait it out. A few things that can help break the silence:

• Send a value anchor, not just a check-in. Instead of “just following up,” reconnect with something specific: “When we talked in discovery, you mentioned X was costing your team Y hours a week. Wanted to make sure that’s still top of mind as you’re evaluating.” It’s harder to ignore than a generic nudge.

• Make it easy to respond. Sometimes silence really is just busyness. A simple “just a yes or no - are we still on track to move forward this month?” removes the friction of composing a full reply.

  • 💡 Pro-Tip: Most of my AEs also communicate with many of their prospects via text, which can be a game-changer. In addition to making communication super easy, it also adds a layer of casualness, which you can use to your advantage! You know your deals best - only use this with contacts where it makes sense.

• Loop in another contact. If you’ve been talking to one person and they’ve gone dark, reach out to another stakeholder you’ve built rapport with. You’re not going around your contact; you’re making sure the deal doesn’t get lost in someone’s inbox. I’ve said it once, and I’ll say it a 100 more times - never let your deal die with one person.

• Know when to call it. If you’ve followed up multiple times across multiple channels with zero response, it’s okay to send a “closing the loop” note, aka a “breakup” email. You can send something like: “I don’t want to keep reaching out if the timing isn’t right. If I don’t hear from you by the end of the week, we’ll go ahead and close out your file.” It’s professional, it preserves the relationship, and sometimes it’s exactly what prompts a response. You’d be surprised by how many times this has brought people back (I don’t always understand it either 😂).

🧰 Know Your Resources

Now I want to talk about resources, and I want to be really clear here: these are not Hail Marys. If you’ve run your process well, you shouldn’t need to call in favors to save a dying deal. But wild things happen in sales (don’t we all know it), and sometimes, deals that were sailing fine start taking on water for reasons completely outside your control. This is when you reach into your toolbox. A few strategies that I’ve seen work well:

• Top-to-top outreach. Ask your manager or executive sponsor to send a quick note to their counterpart. This shouldn’t be a pitch, but rather a short, warm “we’re excited to work together and wanted to make sure you had everything you need” email. It reaffirms commitment at a higher level and can move things along when an AE’s relationship alone isn’t enough to break through.

• A reference call. If a prospect is on the fence, hearing directly from a happy customer can do what no deck ever could. Have a few reference customers you trust in your back pocket who are willing to have a 15-minute conversation (work with your Customer Success team here - they can be amazing partners). Don’t overuse this one, but when the timing is right, it’s incredibly effective.

• A deal-specific concession. I’m not talking about just discounting to get a deal done (👹 never negotiate against yourself 👹). But if there’s a meaningful objection around terms, scope, or implementation timeline, sometimes a targeted, time-bound concession can be the nudge a deal needs. Just make sure it’s a real one, and not a fake urgency play.

  • Fun horror story: I once had a buyer tell one of my reps, “I’m not worried about losing this discount because I know you’ll just honor it next month.” 💀 You can bet we never ran that move ever again.

• A live ROI revisit. Sometimes all it takes is reconnecting the dots between where they were when you started talking and where they are now. Pull up the pain they shared in discovery and tie it back to what you built together. Remind them why this was worth solving in the first place.

The thread through all of these: they work best when they’re planned and intentional, not reactive and desperate. Know your resources before you need them.

🤝 Part 2: The Handoff (and Why It Actually Matters)

Okay. The signature is in. You did it! 🎉

Time to move on to the next deal and never think about this person again, right? I wish. Jk, CS team.

One of the most common mistakes I see from AEs is treating the close like the finish line. For your prospect (who is now your customer, btdubs), it’s the starting line. If they feel like you dropped them the second the contract was signed, you can create a negative impression about you and your company for a long time after. Renewals, expansions, referrals...all of those live downstream of how the handoff goes.

Here are a few pro-tips you can utilize as you pass the baton:

• Set expectations before you get there. Toward the end of the deal process, let your prospect know what’s coming. Something like: “Once we’re signed, you’ll be introduced to your Account Manager and Customer Success Manager. Here’s what the first few weeks typically look like.” can go a long way. This prevents confusion (and disappointment if they really like you…which they should, hopefully 😅) when you’re handing off the deal.

• Set up a kickoff call (and show up to it). Yes, even after you’ve handed them off to the next team. At a minimum, pop in for the first few minutes to make the introduction in person. A warm intro from the person they’ve been building trust with matters a lot. Don’t just forward an email. Give your AM and CSM a real runway to start the relationship strong.

  • 💡 Pro-Tip: Be clear with your customer that you’re passing the baton. I know it’s tempting to stay involved, especially after you’ve spent weeks (or months) building a real relationship with these people. But hovering after the handoff actually does more harm than good. Every time a customer routes a question through you instead of their AM or CSM, you’re slowing things down and unintentionally undermining the authority of the people who are now responsible for their success. Your AM and CSM need to be the experts in the room from day one. The best thing you can do for your customer at this point is to make sure they know exactly who to call and trust that person completely. A clean exit is a gift to everyone.

• Write a handoff doc. This doesn’t have to be a novel, but it should cover the key things your AM and CSM need to walk in with context, such as:

  • The core pain points the customer came in with

  • What was covered in the trial, and what results they saw (or didn’t see)

  • Any expectations that were set around the product, timeline, or support

  • Key stakeholders and their personalities (Who is the champion? Who was skeptical? Who signs off on the renewal?)

  • Any commitments you made that need to be followed through on

• For enterprise deals, start even earlier. If you’re working a larger opportunity and things are progressing well, consider creating a shared Slack channel and adding your AM and CSM before the deal closes. That way, they have context, they can follow along as the deal develops, and the introduction to the customer is genuinely warm because they already know the story. It also signals internally that this is a team effort, not just an AE’s solo win. We’ve even had AMs/CSMs join calls with larger companies before the deal closed to show the prospect we’re a unified front and that we take their care seriously - they’ll be looked after long after signing and are truly our partners, not just numbers on a P&L.

Sales is a team sport. Everyone wins together, or everyone loses together. The handoff is where those relationships get built (or broken), so give your post-sale team the gift of a clean handoff. They’ll remember it.

💭 Closing Thoughts

We covered a lot of ground in April. If there’s one theme I’d pull across all four of these, it’s this: the best deals are run with intention and drive. The reps who close consistently aren’t just talented. They’re prepared, they stay engaged through the finish line, and they treat the post-sale relationship as part of their own reputation. It’s easy to celebrate the close and move on. It takes a little more discipline to see the deal all the way through the door.

Speaking of what’s next...a lot of you have been asking about ramping BDRs and AEs. How do you onboard people well? How do you set them up to ramp faster without throwing them into the deep end? We’ll dig into all of it next month. Stay tuned. 👀

Till then, go sell something! 💰

Stacy

📚 Stacy’s Book Challenge

This year’s goal is…81. 1 more than last year. 😮‍💨 Follow along as I try to get there.

As of this post, I have read 26 books. Slow going lately…I finished Pirate Latitudes earlier this week! I’m a huge Crichton fan, though this probably wasn’t his strongest work. I’m currently reading:

• All Quiet on the Western Front - Okay, you guys should be proud of me - I brought this to Paris, and I’m actually almost done with it 😂

• The Sword of Shannara - Still working through this one…it’s still fine lol

• Pachinko - The story is getting interesting, and I found a Netflix drama based on the book, so I’ll be watching that after!

• Dungeon Crawler Carl - Another one that’s been popping up everywhere - it was available on Kindle Unlimited, so I’m checking it out!

Follow me on GoodReads! 🤓

If you’ve been following this month’s series, you know I’m a big believer that every stage of your sales cycle should set up the next one. Discovery informs the demo, and the demo informs the trial. If you’ve done all of that well, presenting pricing should feel like a natural next step. If a prospect is shocked by the number, that’s not a pricing problem (unless your pricing is totally nuts 😅)…that’s a discovery problem. It means somewhere along the way, you didn’t anchor the conversation to business outcomes, or you didn’t quantify the pain enough for the cost to feel obvious.

Even then, buyers do be crazy sometimes.

Objections are part of the sales process. The key is understanding why they’re coming up so you can address the root cause instead of reacting to the surface-level concern.

I covered common issues by stage in Using Pipeline Analysis to Coach Where It Counts. Think of this as the deep dive on what happens when you’re at the 5-yard line. 🏈

❌ Five Common Objections at the Pricing Stage

1. “The price is too high.”

Why this comes up:

Either the prospect doesn’t fully understand the value, or they genuinely have a hard budget ceiling. Two very different problems with two very different solutions.

How to handle it:

• If it’s a value problem, get curious, not defensive. Go back to what you agreed on:

  • “We aligned on X problem costing you $Y annually, and we demonstrated we can solve it. Help me understand what’s changed.”

  • You’re forcing the prospect to validate their math, and also working on getting to the root of the issue.

    • Did they just not really understand the value your product brings? Remind them!

    • Are they undervaluing their time? This is very common (unfortunately). Ask them what other projects they could be doing with the time they’re saving by buying your product.

    • Are they anchored to a competitor’s price? That’s an apples-to-oranges problem. Ask what’s included in that number. Scope, support, implementation? Nine times out of ten, the “cheaper” option isn’t actually cheaper once you compare what’s covered.

    • Is it sticker shock on the absolute number? Sometimes prospects fixate on the total contract value instead of the ROI. Reframe it. “That’s $X per year to recover $Y. What would it cost to solve this problem internally?”

• If it’s a real budget constraint, don’t just cave and throw out a discount. Discounting without changing scope trains your buyers to negotiate harder every time or makes them undervalue your product.

  • Explore a smaller starting point: “What if we started here, proved the value, and found ways to unlock more budget from there?”

💡Pro-Tip: The key question is “Too high compared to what?” The answer will help tease out if you’re dealing with a value gap or a budget gap.

2. “The contract term is too long.”

Why this comes up:

Prospects push back on contract length when they don’t trust that the value will sustain. This objection usually points to a fear of commitment. They’re saying, “What if this doesn’t work out and I’m stuck?” Sometimes it’s procurement policy, but more often than you’d think, it’s emotional.

How to handle it:

• Understand the driver. Ask: “Is this a company policy, or is there a specific concern about being locked in?” Policy = straightforward negotiation. Trust = your real objection to solve.

• Lean on trial results. “You saw a 40% reduction in [problem] during the trial. What would need to be true for you to feel confident committing to a year?” Make them articulate it. That often resolves the concern on its own.

• If they won’t budge, consider a shorter initial term with a built-in expansion trigger, but be deliberate. Every concession should come with something in return. More on this in a sec.

3. “We need to adjust payment terms.”

Why this comes up:

Payment term requests (net 90 instead of net 30, quarterly instead of annual upfront) are sometimes legitimate cash flow constraints and sometimes just another lever to see what moves. The challenge is that payment terms also affect your business directly. So, make sure you’re not blindly agreeing to things just to get the deal in the door. Your finance team will thank you for it. 🥲

How to handle it:

• Treat payment terms as another negotiation variable, not a throwaway concession. If they want net 90, understand why. Is AP genuinely slow? Procurement standard?

• Trade for something. “We can work with quarterly payments. Would you be open to a longer initial term to give us both more predictability?”

• Get finance involved early. Concessions that seem small on one deal can create real problems across a portfolio.

💡Pro-Tip: If your company doesn’t have one already, work with Sales leadership to create a Pricing and Negotiations doc that outlines what AEs are allowed (or not allowed) to offer. This will help cut back on a lot of oopsies and/or back-and-forth internal conversations that may slow your deal down.

4. “I need to run this by my [boss/CFO/board].”

Why this comes up:

The decision maker isn’t at the table. You either didn’t map the buying committee well enough in discovery, or your contact doesn’t have the authority they implied. It’s incredibly common and incredibly dangerous, because now your deal is being represented by someone who isn’t you. 😬

How to handle it:

• Don’t let it become a game of telephone. Your champion is about to pitch your product internally without your deck, your context, or your answers to tough questions. You need to arm them!

• Co-create the internal business case. “What does your [CFO/VP/board] care about most? Let’s build the case around what matters to them.” Give them the ROI summary, competitive context, and risk-of-doing-nothing framing.

• Ask for a seat at the table. “Would it be helpful if I joined that conversation?” You’d be surprised how often they say yes when you frame it as helpful rather than pushy.

• For next time: Build multi-threading into your process earlier. If you’re only talking to one person by the time you get to pricing, you’ve already lost leverage.

5. “We’re also evaluating [competitor].”

Why this comes up:

Sometimes this is true, sometimes it’s a tactic to pressure you into discounting. Either way, the worst thing you can do is panic and start slashing price. 🙅🏻‍♀️

How to handle it:

• Stay calm and get specific. “That’s great. You should absolutely evaluate your options. What’s most important to you in that comparison?”

  • In fact, at SupplyPike, we would actually help our prospects design evaluation criteria or write a list of questions they should ask the competitor. It showed a real commitment to our partnership and confidence in our value prop. When you know you have the best product, you don’t care who your prospect talks to. 😏

• Lean into your results. No competitor deck beats a prospect’s own data. “You’ve already seen what we can do with your data. How does that compare to what they’ve shown you?”

• Never trash the competitor. It makes you look insecure. Ask questions that surface their weaknesses without you having to say it. Let the prospect connect the dots.

• If they’re using competition purely to drive a discount, that’s where your negotiation discipline kicks in. 👇

🌟 Negotiation Principles for the Pricing Stage

Confirm you’re the choice before you concede anything.

Make sure you are the selected vendor before going down the negotiation rabbit hole. Ask: “If we can work through these terms, are we your vendor of choice?”

You need a clear yes before you start moving.

Otherwise, you’ll make concession after concession only to discover they had three more asks behind the first one. Get confirmation that you’re the pick and that these are the only remaining items. Then negotiate.

Every concession needs a return.

Never give something for nothing.

• They want a lower price? → Change the scope

• They want better payment terms? → Extend the contract

• They want a shorter term? → Hold on price

The moment you give without getting, you’ve signaled that your pricing had room in it all along.

Match the energy in the room.

I’ve said it before, and I’ll say it again. People buy from people they like. And likeability at this stage isn’t about being slick, it’s about resonating with your prospect. If they’re buttoned-up and direct, be buttoned-up and direct. If they’re casual and bubbly, loosen up. If they’re skeptical and hardcore, don’t try to charm them.

It’s still important to remain genuine to who you are and how you sell! That said, the best negotiators aren’t necessarily the best talkers. They’re the ones who read the room and adapt.

Know your walk-away line.

Not every deal is a good deal.

This is really hard for a lot of new sellers (and startups) to accept. A signed contract at the wrong terms can cost you more in support burden, churn risk, and internal credibility than no deal at all. Have the discipline to walk away when the math doesn’t work.

Protect the relationship, not just the deal.

A deal has to work for three parties:

1. You (the rep)

2. The customer

3. Your company

A deal where the customer feels squeezed creates potential churn. A deal where you gave away the farm creates resentment internally (ask me how I know 😭). A deal where you hit your number but the customer isn’t set up for success creates problems for your AM team.

A good AE closes the deal. A great AE builds a reputation that lasts long after the confetti clears. 🥳

🤝 Final Thoughts

The pricing stage is where all your earlier work either pays off or falls apart. If discovery was thorough, if the demo was tailored, and if the trial proved value, then pricing is a conversation, not a confrontation.

Alas, objections will still come up…they always do. But when you understand why they’re surfacing, you can address the real concern instead of just reacting to the words. This isn’t just about “winning” the negotiation (though I know that feels good too). It’s about building a deal where the customer sees clear value, your company is protected, and you’ve set the stage for a long-term relationship, not just a signed contract.

Next week, we’ll wrap up our AE series with tips on closing the deal and setting up your AM and CS teams for success. 🥹

Till then, go sell something! 💰
Stacy

📚 Stacy’s Book Challenge

This year’s goal is…81. 1 more than last year. 😮‍💨 Follow along as I try to get there.

As of this post, I have read 25 books. Not a ton of progress since last week…I finished Gone Girl! I’ve seen the movie but had never read the book. It was a LOT of fun. I need to read more Gillian Flynn! I’m currently reading:

• All Quiet on the Western Front - I told y’all…don’t say nothin’ 😂

• The Sword of Shannara - Still working through this one…it’s still fine lol

• Pachinko - I’ve seen this pop up everywhere, so finally decided to pick it up - another big book, but really strong writing so far!

Follow me on GoodReads! 🤓

🖥️ One Quick Note

As with most of WRT, Christine and I write from the perspective of a B2B SaaS company. Everything in this article assumes you have a working demo environment or a live product you can actually show prospects. If you’re not there yet, pause! 🛑 We’ll be partnering with our friends in Product over the next few months to share some guidance on running product discovery meetings so you can build toward product-market fit from the start. Stay tuned for that!

Without further ado, let’s hop in! 🦘

🎯 The Demo: Show What Matters

Here’s an unfortunate truth about demos - most reps treat them like a presentation. They show up to the call, pull up the deck (I have a lot of thoughts about decks…more to come one day), cover their script, check the boxes, and call it a day. The best reps treat demos like a continuation of the discovery conversation. When you’ve done discovery well, you already know the two or three things keeping your prospect up at night before you even open your laptop. The demo is where you connect those pain points directly to your product.

⭐️ Average AEs run a feature tour. They show every tab, every dashboard, and every button, hoping something lands. I’ve watched reps spend 20 minutes clicking through parts of the product the prospect will literally never use because it’s not relevant to their role or the pain points they’ve brought up. When the call ends, the prospect says, “Yeah, this looks interesting!” and then you never hear from them again.

⭐️⭐️ Good AEs run a pain conversation, with the product as the evidence. The framing looks completely different. Instead of “let me walk you through the product,” it’s “you mentioned that your team is spending hours every week pulling reports manually. Here’s exactly how we fix that.” Every single thing they show connects back to something the prospect told them they care about.

⭐️⭐️⭐️ Great AEs vision cast. Beyond tying the product to a pain point, they pause and make the prospect imagine their life with it (or without it 👀). “What do you think about that? How would that change things for your team?” They’re not just demonstrating the product; they’re helping the prospect sell it internally before the call even ends. When a prospect starts saying things like “oh, this would be huge for Sarah in finance” or “we could finally get rid of that spreadsheet we’ve had since 2019”...you’ve got ‘em.

A few other things that help:

• Use their words back to them. Pay special attention to the terminology/jargon that your prospect uses. If your company calls it “hiring”, but your prospect calls it “headcount planning”, switch your language to say “headcount planning”. You’ll spend less time “translating” and more time connecting. It may seem small, but it signals that you’re actually listening.

• Skip what isn’t relevant. This one can be tough, especially for founder-sellers who are showing off their baby. Showing a barrage of features that don’t connect to your prospects’ pain doesn’t make you look thorough - it makes you look like you weren’t paying attention. Watch their body language. If their eyes are glazing over, it’s time to move on. A shocking number of AEs go into “checklist mode” and basically black out when presenting. Don’t do this. 😭

• Pause and check in after each section. Don’t just demo at them. After you walk through something, ask: “Does this solve what you were describing?” It keeps it a conversation, not a monologue, and it tells you in real time whether you’re landing or if you need to pivot.

🧵 A Note on Multi-Threading

If you have multiple stakeholders on the call, your demo needs to speak to all of them. Different people feel different pain.

The ops person cares about process. The finance person cares about cost and ROI. The end user cares about whether the product makes their day less painful. You don’t need to run three separate demos, but you do need to make sure you’ve said something meaningful to everyone in the room. I’ve sat in on demos where people have introduced themselves and never get spoken to or referenced ever again. 👹 Another big no-no.

A simple way to do this: at the start of the call, ask each person what they’re most hoping to see. Then reference those answers throughout. “Sarah, this is the part you mentioned you were curious about.” When everyone leaves feeling like the product spoke to their specific problem, you’ve created buy-in before the trial even starts. That’s a really good place to be.

🧪 The Trial: Run It Like a Project, Not a Free Sample

So let’s say you crushed the demo (of course you did!). They’re in. They want to trial. Now what?

If you’re not careful, this is where deals can start to fall apart. The AE sets up the trial, sends over credentials, and then checks in once a week with a “hey, just checking in, how’s it going?” The prospect pokes around for a few days, gets busy, and by week three, they’ve barely touched it. When the trial ends, you hear: “We didn’t really get a chance to dig in.” or “It didn’t really do what we thought it would.” And then the deal slips a quarter and eventually dies.

A well-run trial is a managed experience. Here’s how to do it.

✅ Before the Trial: Bring Alignment

Do not kick off a trial without agreeing on success criteria first. Both sides need to know what you’re trying to prove. This will also help to prevent your prospect from moving the goal posts later.

“We want to see if it helps with reporting” is not a strong success criterion. Something like this is:

“We want to confirm that a manager can pull a weekly inventory report in under five minutes, without pulling in IT.”

Get that specific. Then write it down and send it to them. It becomes the North Star for the entire trial and makes the end-of-trial conversation infinitely easier. (More on that in a second.)

• 💡 Pro-Tip: Get the check-in meetings on the calendar before the trial kicks off. If those meetings aren’t booked before the trial starts, you’re hoping the prospect drives momentum. And they won’t. I say this to my AEs all the time: Remove the barriers to a yes. Help them help you! You need, at a minimum:

  • A kickoff call to walk them through the setup and confirm the success criteria together

  • A midpoint check-in to check on progress and pivot if needed

  • An end-of-trial review where you present what was proven

📝 At the Midpoint: Bring Specifics

Check in on actual usage. Are they logging in? Are the right people using it? If engagement is low, that’s your signal to step in right then, not at the end when it’s too late.

Ask things like: “What have you been able to test so far?” and “Are we on track to prove X by the end of the trial?” If the answer is no, figure out why and fix it together. Maybe they need a training session. Maybe the wrong person was set up as the admin. Maybe they just need a nudge. Whatever it is, you can only fix it if you’re asking.

🧾 At the End: Bring Receipts

At the end of the trial period, don’t just walk in and ask them what they thought. Bring a summary of what was done and what was proven. If you can pull usage data, pull it. If you can show how their specific use case played out in the product, show it.

Then anchor the whole conversation back to what they told you they needed to see: “You said success was X. Here’s how we delivered on that.” That’s a very different conversation from hoping they remember why they liked your app.

• 💡 Pro-Tip: Be cautious of scope creep and roadmap promises, especially in the early days. During trials, buyers sometimes ask about features that don’t exist yet. And reps, wanting to keep the energy up, say “that’s on the roadmap!” Be careful here. The second the deal depends on something that doesn’t exist yet, you’ve introduced risk. Anchor the value conversation in what the product does today. If a new pain surfaces mid-trial that’s legitimately worth exploring, great! Dig in. Just make sure it’s deepening the value story, not replacing it.

💰 Why All of This Matters

Everything you do in the trial is setting you up for the pricing conversation, which is usually the next step.

When you’ve defined success criteria together, hit them, and documented the proof, you’re not walking into pricing cold. You’re walking in with a case. Think about how different these two conversations sound and feel:

• Version A: You send over pricing, hope they remember why they liked the demo three weeks ago, and wait to see what happens.

• Version B: “You told us visibility was costing your team 10 hours a week. Here’s what we proved during the trial. Here’s what that investment looks like in order for you to take advantage of that.”

One of those conversations puts you at the mercy of the prospect’s memory and mood. The other puts you in control. The trial isn’t just a proof of concept. It’s your setup for the close. Treat it that way.

💭 Final Thoughts

Running the demo and the trial can sometimes be two of the most underrated skill sets in SaaS sales. Everyone wants to talk about prospecting and closing, but the middle of the deal cycle is where reps can separate themselves from being okay to being great. I’ve seen strong discovery get completely squandered by reps who treat the demo like a product tour or drop a prospect off for a trial and then try to present pricing without ever checking in. Don’t be that person. 🙅🏻‍♀️

Show what’s relevant to your prospect, not what’s fun for you. Vision cast. Make them imagine their life with your product before the call even ends. Then run the trial like a project: clear success criteria upfront, structured check-ins, and an end-of-trial review where you walk in with actual proof. If you do all of that well, the pricing conversation stops feeling like a negotiation and starts feeling like a formality.

Next week, we’re getting into presenting pricing and overcoming common objections, before we wrap up with closing the deal and passing it on to the Customer Success team. 🤝

Till then, go sell something! 💰
Stacy

📚 Stacy’s Book Challenge

This year’s goal is…81. 1 more than last year. 😮‍💨 Follow along as I try to get there.

As of this post, I have read 24 books. I finished The Correspondent, which was…overrated. Don’t come at me! I also finished This Story Might Save Your Life. It had an interesting first half but just fell apart in the second. Don’t waste your time with it.

I wrapped up Bright Young Women, which was also…okay. Strong plot, writing wasn’t great imo. Finally, I finished I Who Have Never Known Men, which was easily my favorite read of the week. Really interesting plot about a group of women who’ve been trapped in an underground bunker and don’t remember how or why they got there. Highly recommend if you’re looking for a short, powerful read. 👀

I’m currently reading:

• All Quiet on the Western Front - At this point, no one say nothin’ lmao

• The Sword of Shannara - I mean…it’s fine - my husband really wants me to read this, so I am 😂

• Gone Girl - I’ve seen the movie but haven’t read the book yet! So far, so good!

Follow me on GoodReads! 🤓

• 🔍 Discovery: Uncovering real pain and setting the foundation for the sales cycle

• 🎙️ The Demo: Turning what you learned into a conversation that sells

• 💰 Objections & Stalled Deals: Navigating negotiations

• ✍🏼 The Close: Getting to yes with confidence

This week, we’re starting where every deal should: discovery.

Discovery isn’t just the first call. It’s the foundation on which everything else gets built. 🏗️ Your demo only lands if it’s anchored in what you learned. Your pricing conversation only sticks if the value is already established. Your close is nearly impossible if you don’t know what actually matters to the buyer. When discovery is weak, the rest of the cycle feels like pushing a boulder uphill. So let’s talk about how to do it well!

🪏 Dig Deep: Go Beyond the Surface Pain

Most AEs are pretty adept at finding pain. The prospect says, “Our current process is really manual,” and the AE nods along, checks a mental box, and moves on or tries to find a feature to call out that fits the pain point. While surface pain can be a great place to start, what you’re actually looking for is the why behind the why.

When someone tells you their process is manual, that’s the beginning of the conversation, not the end. It’s a great signal for you to push deeper:

• “What does that cost you? In time, in headcount, in dollars?”

• “Who else feels that pain, and how does it show up for them?”

• “What happens if this doesn’t get fixed in the next six months?”

Questions like these force the prospect to think through consequences, not just frustrations. And consequences are what drive urgency. “Yeah, reporting is kind of a pain” is very different from “If we don’t fix this by Q3, we’re going to miss our board reporting deadline, and that’s going to be a really bad conversation.”

Your job is to get to the second outcome, and the way you get there is by staying genuinely curious instead of rushing toward a solution. The more you let them talk, the more they’ll tell you.

❓ Questions Worth Asking

You don’t need a custom script for every product. In fact, I’ve found conversations to feel stilted and stiff when AEs try to memorize things to say. There’s a core set of discovery questions that work across almost any B2B sales cycle, which you should try to weave into your conversations. Of course, make them sound natural to you and the conversation!

• “Walk me through what your current process looks like today.”

• “What’s working about it? What isn’t?”

• “How long has this been a problem?”

• “What have you tried to fix it? What happened?”

• “What does success look like for you, specifically, 12 months from now?”

• “Who else is affected by this problem inside your organization?”

• “What would need to be true for you to move forward with something like this?”

• “Is there a timeline driving this decision?”

The questions in and of themselves won’t close the deal (a girl can dream). What matters is what you do with the answers. Take notes actively and visibly. Even on a video call, saying “I’m going to write that down” signals to the prospect that what they’re sharing actually matters to you. Then use it. Reference it back later in the call, in your follow-up email, and throughout the rest of the sales cycle.

💡Pro-Tip: These days, almost every B2B SaaS org equips their team with call recorders or note takers (Gong and Chorus are a few that come to mind). I mentioned it in a previous article, but these days, there’s almost no excuse for sellers not to know or remember what was said in calls. Use your prospect’s language with them - it will absolutely help you to stand out!

💡Another Pro-Tip: Send a prep email before the call. A quick note that says “Here’s what I’m hoping to cover and learn. Do you agree or want to cover anything else?” accomplishes two things. It sets expectations so the prospect comes prepared, and it positions you as someone who takes their time seriously. It doesn’t need to be long. Three bullet points are fine. It also may give you a hint into where their head is at if they’re asking to cover specific topics.

👥 Know Your Personas (and Use Them)

Different people at the same company have completely different pain points. And if you’re only talking to one person, you’re only seeing one part of the deal.

I’ll give you a simple example. Let’s say you’re selling a campus scheduling and operations platform to a university. You’re not selling to “the university.” You’re selling to a whole cast of characters, each with their own version of the problem.

The IT Director cares about security, integrations, and how hard this will be to maintain.

• Their questions sound like: “Does this connect to our existing systems? Who owns it when something breaks?”

• For them, discovery sounds like: “Tell me about your current tech stack. What would make a new tool a nightmare to implement?”

The Registrar cares about scheduling conflicts, room utilization, and student complaints. Their pain is operational.

• Their questions sound like: “Can we see real-time availability? What happens when there’s a double booking?”

• For them, discovery sounds like: “Walk me through what a typical scheduling week looks like during peak registration. Where does it usually break down?”

The VP of Finance or a Budget Owner cares about ROI and whether this eliminates headcount cost or reduces overtime.

• Their questions sound like: “How much will this cost? Is this worth my investment?”

• For them, discovery sounds like: “How many hours per week do you estimate your team spends on manual scheduling tasks? What does that translate to in labor costs annually?”

Three personas. Three completely different conversations. If you’re not strategizing different approaches to each person, you stand a chance of losing the deal behind the scenes.

This concept is called multi-threading, and it’s one of the most underutilized deal strategies out there. When you understand what matters to each stakeholder, you have multiple angles to create value and urgency. If your champion goes quiet, you have other relationships. If budget gets questioned, you have the finance angle ready. Multi-threading also protects you later in the cycle when new stakeholders surface. If you’ve already talked to procurement or legal’s equivalent at the organization, there are no surprises. I preach this to my team literally every day: do not let the deal die with one person.

A good rule of thumb: by the end of your discovery phase, you should be able to clearly articulate the pain and the stakes from at least two different personas’ perspectives. If you can’t, you probably have more discovery to do.

📚 A Note on Sales Methodologies

Once you start thinking in personas and pain points, you’ll start to notice that there’s a structure underneath good discovery. That’s essentially what sales methodologies are trying to capture.

You may have heard terms like MEDDICC, MEDDPICC, Challenger, SPIN Selling, or others. These are frameworks designed to help you think more rigorously about your deals and your buyers. They’re certainly worth exploring, especially if you’re newer to sales.

For example, MEDDPICC is one of the most commonly seen sales frameworks in SaaS and gives you a clear map of what you should know about any deal before it gets too far along. MEDDPICC stands for…

• Metrics: The quantifiable impact your solution delivers (time saved, revenue gained, cost reduced)

• Economic Buyer: The person who controls the budget and has the final say on the deal

• Decision Criteria: The requirements and standards your buyer will use to evaluate their options

• Decision Process: The internal steps, approvals, and timeline required to get a deal signed

• Paper Process: The legal, procurement, and contracting steps that happen after a decision is made

• Identify Pain: The core business problem driving urgency and the cost of leaving it unsolved

• Champion: Your internal advocate who believes in your solution and will sell it when you’re not in the room

• Competition: Who else is being evaluated, and what you’re up against to win the deal

You don’t have to pick one and live by it religiously (unless your RevOps team tells you to 😂). But if your deal reviews feel fuzzy or you struggle to articulate why an opportunity is real, these frameworks are a great starting point to “force” discovery. In my experience, the reps who know their deals best have internalized at least one of them. Even if they never say the acronym out loud, you can hear it in how they talk about their pipeline.

🤝 The Art of Sales

This one feels pretty obvious, but you might be surprised.

I once sat in on a discovery call where the AE had built a fully formatted PowerPoint slide with a bulleted list of discovery questions…and they shared their screen and walked through it. With the prospect. 💀

The prospect was polite about it. But there was zero warmth, zero conversational flow, and absolutely no trust built on that call. It felt like an interrogation, not a conversation.

People buy from people they like. I know I do. The best discovery calls don’t feel like discovery calls at all. They feel like two people genuinely trying to figure out if there’s a problem worth solving together. And here’s a soft pro-tip: sometimes there isn’t! My team is great about telling prospects when working with us doesn’t make sense. 🤯 It feels contradictory, but it signals to the prospects that we care about their outcomes - not just ours. We’ve had a surprising number of folks actually say they wanted to work with us regardless! Again, people buy from people they like!

Some things that can help with tone:

• Share a little bit about yourself. I know, I know - small talk can feel cringey. But in this day and age, all of us are on Zoom calls at least 10 hours a week. I encourage my team to be the best call their prospect has to get on for the day - they should look forward to talking to you!

• Do your research beforehand. Find something real to reference about their business or their role. It signals that you showed up prepared, and it gives you a natural, low-pressure way to open the call before you get into the heavy stuff.

• Let there be silence. When you ask a big question, resist the urge to fill the pause. Let them think. Let them talk. The best insights come from the moments after the first answer.

• React like a human. If something they share surprises you or resonates, say so. “That’s actually more common than most people realize,” or “I haven’t heard it framed that way before” goes a long way.

• Weave questions in, don’t fire them out. Build on what they say. Let the conversation breathe. You’re not running through a checklist - you’re having a dialogue.

• Close the call with a clear next step. Discovery shouldn’t end with “Great, I’ll follow up with some info.” It should end with a specific next step that both parties have agreed to. “Based on what you shared, I’d love to put together a demo focused specifically on X. Can we get 30 minutes on the calendar for next Thursday?”

Your personality is an asset. If you’re a sports person, talk about sports. If you’re a proud parent, mention your kids. If you’re naturally bubbly and high-energy, bring that energy into the call. The goal isn’t to be likeable in a performed way. It’s to just be yourself: curious, present, and genuinely interested in the person on the other side of the call. Some of the best sellers I’ve worked with have wildly different personalities. What they all have in common is that they show up as exactly who they are, every single time.

💬 Final Thoughts

Discovery is where deals are won or lost, long before anyone ever sees a contract. It’s where you earn trust, uncover real pain, build urgency, and start to understand whether this is actually a deal worth pursuing.

Get this part right, and everything that follows gets easier. We’ve talked before about what shallow discovery looks like from the manager’s seat (if you missed it, check out Using Pipeline Analysis to Coach Your Team). This is the rep’s version of that same story.

Next week, we’re turning those discovery insights into a demo that actually sells. 👀

Till then, start asking those questions!
Stacy

📚 Stacy’s Book Challenge

This year’s goal is…81. 1 more than last year. 😮‍💨 Follow along as I try to get there.

As of this post, I have read 20 books. I finished Lonesome Dove, and omg. Another 5-star Western for me this year! 🤠 It’s so not my usual genre, but what a journey. I think this may be one of my Top 5 books of all time. Gus and Call, my heart belongs to you!

I also finished Revenge (aka The Stars’ Tennis Balls) - great if you want a book that’s…well…about revenge. I also completed If You Can’t Take the Heat: Tales of Food, Feminism, and Fury, and as mentioned last week, non-fiction just really isn’t my jam. So…it was fine.

I’m currently reading:

• All Quiet on the Western Front - I found the book LOL - restarting it this week!

• Bright Young Women - I thought this was the book version of Promising Young Woman…yeah, it’s not that 😮‍💨

• This Story Might Save Your Life - got this in my recent Book of the Month subscription!

• The Correspondent - I’ve seen this title pop up in tons of places, so I thought I’d give it a shot - interesting format, it’s a story told solely through letters

Follow me on GoodReads! 🤓

As sales teams grow, the stuff that used to get sorted out over a quick conversation or Slack huddle can quickly start turning into real-life friction. Handoffs get messy, account ownership feels confusing, and nobody’s quite sure who gets credit when a deal touches multiple people. None of that necessarily means your team is broken. It just means the rules haven’t been written down yet. 📝

That’s what a Rules of Engagement (ROE) doc is for. It provides clear guidance about how your teams should interact with each other, how handoffs work, and who owns what. Think of it as the connective tissue between roles.

Every business is different. So, instead of giving you a one-size-fits-all doc, I wanted to walk through a framework you can use to build your own ROE! For each section, I’ve listed out the key questions your doc should answer. If you can’t answer one of them clearly today, that’s a good sign it needs to be discussed and documented.

Let’s dive in! 🐬

📘 Section 1: Definitions

Before you get into the rules, it’s important to get everyone on the same page about what key terms actually mean at your company. This sounds basic, but I can’t tell you how many arguments I’ve seen that boiled down to two people having different definitions of the same word. 😮‍💨

• What’s a “lead” vs. an “opportunity”?

• What qualifies as an “existing customer” vs. a “new logo”?

• What does “account ownership” mean, and how is it different from “territory assignment”?

• What counts as a “referral” vs. a “partner-sourced” deal?

• If your team uses terms like MQL, SQL, SAL, or PQL, what does each one mean in your context?

• How do you define segments (for example, SMB, Mid-Market, Enterprise), and where are the boundaries?

• What’s the difference between an “upsell” and a “cross-sell” at your company, and who owns each?

• What does “active engagement” on an account look like vs. passive ownership?

This section doesn’t need to be long, but it needs to be airtight, and requires alignment across your entire org. If there are already debates here, go no further - hash it out with the right leaders and then get into the rest.

🔁 Section 2: Handoffs

This is usually where most of the friction lives, so I’d spend some extra time on this section. If roles, responsibilities, and expectations aren’t clearly defined between teams, handoffs get sloppy, and people start pointing fingers when things don’t go well. A few common handoffs in most B2B SaaS companies include:

BDR to AE:

• What does a “qualified” handoff look like? What info needs to be captured before a meeting gets booked?

• What’s the expectation for AE follow-up timing after a handoff?

• If the meeting no-shows or gets cancelled, who re-engages?

• If the BDR-sourced lead goes dark after the handoff, does it ever route back to the BDR?

• If a BDR qualifies a lead but the AE determines it’s not a fit, what happens next? Does the BDR still get credit for the activity? Who makes the final call?

AE to AM/CS:

• At what point does a closed deal transition to an Account Manager or CS team? Contract signature? After onboarding?

• Is there a defined overlap period where both parties are engaged?

• Who owns communication/onboarding activities with the customer during the transition?

• What information does the AE need to hand off (key contacts, context on the sale, promises made, etc.)?

• If a customer brings up expansion interest during onboarding, who picks that up? How long do they have that opportunity for?

• What’s the process if the AM uncovers that something was misrepresented or over-promised during the sales cycle?

Inbound vs. Outbound:

• If a BDR is actively working an account outbound and an inbound lead comes in from the same company, who gets it?

• What’s the tiebreaker? Timestamp? Activity volume? First meaningful engagement?

• How is this tracked in the CRM so it’s not a “he said, she said” situation?

• Is there a lookback window? For example, if the BDR contacted the account within the last 30 days, do they keep it? does there need to be two-way communication for this to count?

A pro-tip here (in addition to ensuring leadership alignment) is to always keep your North Star metric/goal in mind. When you’re unsure how to proceed, ask: How will this decision help or hurt the business? Of course, you want to be as fair as possible to the reps that are involved, but make sure you don’t spend too much time trying to make everyone happy. At the end of the day, you have a responsibility to the business - act accordingly.

🗺️ Section 3: Territories and Account Ownership

Territory and account ownership questions tend to feel straightforward until they’re not. 😬 Who owns what, how long do they own it, and what’s expected of them while they have it? These are three separate but equally important questions, and getting vague on any of them is a fast track to internal drama (don’t ask me how I know…).

Territories:

• How are territories segmented? Geography, company size, vertical, named accounts, or some combination?

• What happens when an account doesn’t fit neatly into a segment?

• How often are territories rebalanced, and what triggers a rebalance?

• If a customer moves locations or changes size tier, does the ownership change?

• Are there any “house accounts” that no individual rep owns? Who manages those?

Account Ownership:

• Does an AE own an account indefinitely, or is there a time limit?

• If a rep hasn’t engaged an account in 60/90/120 days, does it go back into the pool?

• If an AE leaves the company, how are their accounts redistributed?

• Can reps voluntarily release accounts they’re not actively working? Where do those go? Back into the pool or to a rep of their choice? Does the manager have to approve?

• If a rep gets promoted or moves to a different segment, what happens to their existing book?

• When new accounts enter the CRM (e.g., from marketing or product-led signups), what’s the routing logic?

Activity Expectations:

• What level of engagement is required to maintain ownership? (Touches per quarter, updated CRM notes, etc.)

• What quality level is expected for engagement? Can it be a “just checking in” email?

• Who audits this, and how often?

• What happens if a rep isn’t meeting the activity bar? Warning first, or automatic reassignment?

• What does “good standing” look like in the CRM for an owned account? (Updated contacts, recent notes, accurate deal stages, etc.)

🤝 Section 4: Partnerships and Events

If your company works with channel partners, referral partners, or runs events, you need clear rules around how those interactions impact ownership and credit, because the same prospect can be worked across multiple channels.

Partnerships:

• If a partner brings in a lead, who works the deal? The partner? Your AE? Both?

• Does the AE who owns the territory get credit on a partner-sourced deal?

• What’s the process for registering a partner-sourced opportunity?

• If a deal is co-sold, how is that tracked? What does quota attainment and commission look like?

• What happens if a partner submits a lead for an account that’s already in active play with one of your reps?

Events:

• If a lead comes in from a trade show, webinar, or field event, how is it routed?

• Does the rep who had the conversation at the booth get first right of refusal?

• How long after the event does a rep have to follow up before the lead gets rerouted?

• If the lead came from an account that’s already owned, does the existing owner get it automatically?

• What about marketing-hosted events where multiple reps interact with the same prospect?

💰 Section 5: Credit and Compensation Triggers

Though the ROE is not a comp plan doc, it does need to address the moments where credit gets assigned, because (to no one’s surprise), everyone cares a little bit more when money is involved.

• If a BDR books the meeting and the AE closes the deal, does the BDR get credited regardless of whether their original contact is the signer?

• If an AE closes a new logo and the customer expands later, does the AE get credit on the expansion, or is that fully the AM’s? What’s the cutoff date?

• Does your company support deal splits? If so, what triggers it? What are the rules for getting that approved? What are everyone’s responsibilities to get paid?

• If a customer churns and then comes back, is that treated as a new deal or a reactivation? Who gets credit?

• What happens with credit when accounts are reassigned mid-cycle due to territory changes or rep departures?

You won’t be able to anticipate every single scenario, but covering the most common ones will save you a lot of painful conversations later.

🚨 Section 6: Conflict Resolution and Escalation

Even with the best ROE in the world, gray areas will come up. So document what happens when they do.

• Who makes the final call when two reps both believe they should own an account? Direct manager? Sales Ops? VP of Sales?

• What evidence do reps need to bring to the table? (CRM activity logs, timestamps, email threads, etc.)

• What’s the expected turnaround time for a resolution?

• Is there an appeal process if someone disagrees with the outcome?

• How are decisions communicated back to the reps involved?

• Are conflict resolution outcomes tracked so you can spot recurring patterns? (If the same scenario keeps coming up, that’s a gap in your doc.)

• How often should the ROE be reviewed and updated?

  • 💡 Pro-Tip: I’d recommend at least once a quarter with your sales leadership team in the early days, then move to biannually. It’s important to balance keeping your ROE updated based on new scenarios/business changes, but you also want to prevent changing the rules all the time - this can create confusion and even more chaos as things that were considered rules a month ago don’t apply anymore.

🙂‍↕️ Final Thoughts

A good ROE doesn’t just prevent conflict. It actually makes your team run faster! When reps and managers know the rules, they spend less time debating ownership and more time selling. That’s a win-win for everyone. 🙏

A few things I want to leave you with:

First, don’t build this in a vacuum. Your ROE touches every customer-facing team, so your BDR, AE, AM, and CS leaders should all be in the room when this gets created. If only one team writes the rules, the other teams won’t trust them. Get cross-functional buy-in before you roll it out, and you’ll save yourself a ton of pushback later.

Second, once it’s written, walk your teams through it. Don’t just drop a doc in Slack and hope people read it (hint: they won’t lol). Similar to what I shared in our sales comp doc article, take the time to explain the “why” behind the decisions. When people understand the reasoning, they’re way more likely to actually follow the process. And if something doesn’t make sense to them, that’s good feedback. Listen to it!

Third, you don’t need to get this perfect on day one. Start with the sections that cause the most friction on your team right now, get alignment with your leadership group, and build from there. A living doc that covers 80% of scenarios is infinitely better than no doc at all.

If you’re a manager or leader reading this, congratulations. We’ve written A LOT of content for you over the past few months. You’re welcome. 😂 In April, we’re showing some love to the folks who are actually out there doing the selling. We’ll be spending the month on deal execution, starting with discovery and working all the way through to close. 💥

Happy EOQ! Go hustle! 🏃🏻‍♀️
Stacy

📚 Stacy’s Book Challenge

This year’s goal is…81. 1 more than last year. 😮‍💨 Follow along as I try to get there.

As of this post, I have read 17 books. I finished No Country for Old Men, and it was…okay for me. I really enjoyed the plot, but didn’t like the musings interspersed within. I think I’ll watch the movie this weekend!

I’m currently reading:

• All Quiet on the Western Front - Still haven’t found the book lolol

• Lonesome Dove - I’m about 50% through! 🙌🏼

• Revenge (aka The Stars’ Tennis Balls) - I read this literally two decades ago (don’t ask how old I am…)…it’s a fun modern retelling of the Count of Monte Cristo

• If You Can’t Take the Heat: Tales of Food, Feminism, and Fury - I’ll be honest…non-fiction/essays really aren’t my jam, so I’m kind of suffering through this

Follow me on GoodReads! 🤓

Sometimes, nobody had a great answer, and that made it everyone’s problem.

Today, we’ll be diving into how to build a pricing and negotiations guidelines doc that actually gets used: what to put in it, how to structure approvals, and how to make sure the whole thing doesn’t live and die in a Google Doc that nobody can find. This document won’t prevent every bad deal from happening. But the hope is that it dramatically cuts down on the “how did we end up here?” conversations. More importantly, it gives your AEs the confidence to move fast without having to guess what’s okay.

🎯 Before You Build Anything

Before you write a single line of this doc, you need to get in a room and agree on what you’re actually optimizing for right now. Is it market share? Average contract value? Retention? It’s tempting to say “all of the above,” but that dilutes everything, including what your AEs think they’re allowed to give on. Pick one as your North Star and let it guide the rest. ⭐️

For example, if market share is the priority, you might let your AEs discount by up to 50% because the goal is to get logos in the door with room to expand later. That’s a completely different posture than optimizing for revenue, and if you try to do both at once, you’re already making trade-offs that are hard to explain and even harder to enforce. Your board will likely have a point of view here, so it’s worth bringing them into the conversation.

Two Traps to Avoid

Trap 1: No guardrails. In the early days, it’s (kinda) understandable that you want your AEs to be scrappy and creative. But “no rules” isn’t flexibility, it’s chaos with a time delay. Every rep will negotiate differently, every deal will look different, and your AMs and CSMs will spend half their lives cleaning up promises they had no part in making.

Trap 2: Too many guardrails. The flip side can also be problematic. If a 10% discount requires 4 levels of approval, you will paralyze your AEs. Time kills all deals, and your reps lose leverage every time they have to say, “let me check with my manager’s manager’s manager and get back to you.” Give your people real authority to move appropriately.

📋 What to Include in Your Guidelines Doc

Okay, let’s get into the actual doc. Here are a few key sections that are non-negotiable (Get it? Get it? 😂).

General Pricing Strategy

Keep this short; I’d go with no longer than a paragraph or two. What does your pricing reflect? Are you premium, mid-market, or usage-based? How is pricing calculated? Why do you price this way? This is context-setting so your AEs understand the why behind the guardrails. People follow rules a lot better when they understand where they came from.

Here’s what a simple version of this might look like in practice:

Our pricing is based on the prospect’s annual usage volume. We use this metric rather than seat count or number of features because it’s a much better proxy for the actual size of the business. We don’t publish pricing on our website because a 5-person team and a 500-person team are going to have very different conversations, and we’d rather have that discussion in context. If a prospect asks for a number before you’ve had a chance to scope their needs, work with your manager to provide a ballpark range, but always frame it as a starting point, not a quote.

We are a premium product, and we price accordingly. We are not the cheapest option in the market, and that’s intentional. If a prospect is primarily shopping on price, that’s a signal worth paying attention to. Our best customers are the ones who understand the value and are investing in the outcome, not just the lowest line item on their budget. You don’t need to apologize for our pricing. Know it, own it, and sell the value.

💡 To Display or Not to Display: One thing worth addressing explicitly in this section: Do you show pricing on your website? There’s no universally right answer. Some companies love the transparency (and the self-serve pipeline it creates). Others prefer to keep it off the site so pricing conversations happen in context. Both are valid, but your AEs will be asked either way, so give them a talk track. If pricing is on the site, great. Tell them how to walk a prospect through it. If it’s not, explain why (trial data makes pricing more accurate, pricing varies by use case, etc.) so they can answer confidently instead of fumbling around. “We just don’t put it online” is not a talk track. 😬

💡 Link Your Pricing Sheet: Your guidelines doc and your pricing sheet should reference each other, ideally with a direct link in both directions. Better yet, if your pricing is simple enough, put them on one page. Your AEs shouldn’t have to toggle between three different docs to figure out what to charge someone. The simpler this is to access and use, the more likely it actually gets used.

Discount Approval Tiers

This is the heart of the doc. Write down exactly who can approve what, so nobody has to guess or ask around in the middle of a negotiation. Here’s an example of what this can look like:

Of course, the percentages are yours to decide based on your margins and the priority conversation above. Whatever you land on, make it explicit.

If you allow exceptions outside the normal tiers, define what the process looks like. Who do you email? How fast will you hear back? Vague exception processes almost always become workarounds. People figure out which person will just say yes and go straight to them every time.

💡Pro-Tip: Build your approval process into your CRM or Slack if you can. The harder you make it for your AEs to get approvals, the slower deals move. That said, you also can’t have everything living in DMs. If a discount was approved three weeks ago and you need to find it for additional context or to share with the post-sales team, it shouldn’t require scrolling through a sea of messages to locate it. Visibility matters just as much as speed. More on building a Deal Desk below. 👀

Payment Terms

Loop in your finance team before you write this section. Seriously. Your CFO has strong feelings about payment terms, and they should. If you can’t float cash for 60 days, you shouldn’t be handing out Net 60 as a default negotiation concession.

Document your standard terms and the flex points clearly. For example:

Again, the above is simply an illustration of what this can look like. Update this as appropriate for your company.

One thing worth noting: as you move upmarket, you may find yourself adding nuance for enterprise clients. At SupplyPike, for example, we became willing to extend payment terms beyond our standard for contracts over a certain threshold, because the revenue was worth the float.

Accepted Payment Methods

This one sounds obvious, but it’s worth a dedicated line in your doc, and another conversation with your CFO. Do you accept ACH? Credit card? Check? All three? Each comes with tradeoffs your finance team cares about (processing fees, timing, reconciliation headaches), and your AEs need a clear answer when a customer asks.

You can provide guidance as simple as:

• We prefer ACH and credit cards. Checks are technically accepted, but they’re slow and create extra work on the back end, so we don’t lead with them.

Whatever your list is, write it down. And if there are any methods you actively want to avoid, say so explicitly so your AEs aren’t accidentally telling customers “sure, whatever works for you!” and having to walk that back mid-close. No bueno. 🙅🏻‍♀️

Non-Negotiables

Every company has a list of things they just won’t do. Write them down.

Common ones to consider…

• No term-for-convenience clauses: The customer can cancel the contract at any time, for any reason, without penalty. If this is in your contract, your customer essentially has a month-to-month subscription, not an annual commitment.

• No uncapped SLA credits: There is no limit to the financial credits a customer can claim if you miss a service level agreement. This can get very expensive, very fast.

• No custom security reviews for sub-threshold deals: One-off security questionnaires that require significant internal resources to complete, typically requested by enterprise buyers. These are fine above a certain deal size, but not worth the lift on smaller contracts.

• No perpetual licenses: The customer owns the software outright forever, rather than paying for ongoing access. This is almost never in a SaaS company’s interest.

A written list of non-negotiables also gives your AE real cover in the room. “That one’s just not something we do” lands completely differently than “I don’t think so, but let me check.” That confidence matters in a negotiation.

Contract Terms

A few more things worth locking down:

• What you’ll offer on multi-year deals and who approves it.

  • Pros: The customer is locked in for a longer period of time.

  • Cons: Often, the concession is a big discount or the inability to increase pricing in Year 2.

  • This can be worth it, depending on what you’re optimizing for. Work with your finance and customer success teams accordingly!

• Your auto-renewal language and whether it’s negotiable.

  • Along with that, how much notice is required for a customer if they don’t want to renew? Who needs to approve exceptions to that?

• What happens when a customer wants to expand mid-contract?

  • Is that an addendum? Do they sign a new contract? Are different discounts available since they’re a customer?

These come up constantly, and if I haven’t said it enough…making sure your decisions are documented clearly will save you (and your AEs) so much pain in the future.

If your legal or finance team has standard redline guidance on what you will and won’t accept in contract markups, link to it or summarize it in the doc as well. The faster your AEs can get to a real answer, the faster things close.

🗂️ Building a Deal Desk

A deal desk is essentially your internal approval hub: the place where discount requests, custom terms, and exception asks get submitted, reviewed, and documented. At early-stage companies, this doesn’t need to be fancy.

Some teams run this through their CRM, which works well if your CRM has approval workflow capabilities baked in. The upside is that everything lives where the deal data already lives. The downside is that CRMs can miss a lot of context. The nuance of why a discount was requested, what the customer pushed back on, what was discussed, and ultimately what was agreed (or not agreed) to.

SupplyPike actually uses Slack for our Deal Desk, and I am a big fan. Slack lets you build simple workflows, where your AE fills out a form, it routes to the right approver, and everyone who needs to see it does. You can tag legal, finance, your VP, whoever the deal requires. And because it lives in a channel (not a DM), there’s a searchable, visible record of what was asked for and what was approved.

Old lady rant. 👵🏼 I actually have strong opinions about DMs for sales discussions. I don’t like them. Quick questions are fine, but any approval request, discount discussion, or negotiation context should live somewhere where the broader team can see it. When an AM or CSM inherits an account, they need to know the context. If that history lives in someone’s DMs, it’s basically gone.

In fact, for our Enterprise deals (or any deal with a lot of complexity or an extended sales cycle), we require our AEs to create a dedicated Slack channel. It becomes a collaboration space, where legal, finance, tech, leadership, and CS can join and get context and give feedback in real time. When the deal closes and is handed off, the channel doesn’t disappear, and the history lives on. You can always mute the channel after close (heaven knows we all have too many Slack channels already), but the knowledge stays alive. Set your teams up for success. 🤝

🏁 Final Thoughts

This doc isn’t about controlling your AEs. It’s about giving them a faster path to yes. When reps know exactly what they can approve, what needs escalation, and what’s off the table, they can negotiate with confidence and stop burning time chasing approvals mid-deal. As with all things…start simple. A one-pager that covers the basics beats a 12-page policy that nobody reads. You can always add nuance as you learn which situations keep coming up that the doc doesn’t address yet, and trust me, they will come up. 😅

Next week, we’re going to talk about how to build a rules of engagement doc. If pricing and negotiations are the “what,” rules of engagement are the “who”: who owns which accounts, how you handle overlapping territories, and how you make sure your AEs aren’t accidentally stepping on each other (or on your CS team). Stay tuned! 👀

Until then, happy discounting! 🤑
Stacy

📚 Stacy’s Book Challenge

This year’s goal is…81. 1 more than last year. 😮‍💨 Follow along as I try to get there.

As of this post, I have read 16 books. I finished Call Me By Your Name and The Johnson Four last week. Both were actually really great. Either I’m getting older and easier to please, or I’m getting lucky with the books I’ve chosen this year. 😂 I also read Heated Rivalry. I mean, I watched the show, but I still wasn’t prepared lol.

I’m currently reading:

• All Quiet on the Western Front - Okay…I’ve actually lost this book. LOL. I need to go find it…

• Lonesome Dove - I made some progress this week! It reminds me of East of Eden…don’t come after me, literary purists!!!

• No Country for Old Men - Another book set in Texas? Maybe this is a sign. All I can think of when I’m reading is Javier Bardem’s hair in the movie.

Follow me on GoodReads! 🤓

Here’s the reality of working at an early-stage startup: things move fast. You’re wearing multiple hats, your team is lean, and when things are flying, updating the CRM can feel like the lowest priority. I know this because I’ve lived this.

The problem is, it catches up with you. Close dates start drifting…dead deals hang around in pipeline way longer than they should…stages stop meaning what they’re supposed to mean. And then one day you’re sitting in a forecast call, and you realize that the pipeline you’ve been planning around doesn’t actually reflect what’s happening. That’s not a fun place to be.

The good news is that keeping your CRM clean really isn’t that hard (yes, really). It just takes a little intention and a few habits baked into your routine. Today, I want to walk through the most common traps I see teams fall into, why they matter more than you’d think, and how to stay on top of it all without becoming that manager who’s nagging about CRM updates every five minutes.

🧠 It’s Not About Being Neat

Let me get this out of the way early: CRM hygiene is not about being organized for the sake of being organized. I’ve seen all the memes. 😭 This isn’t a tidiness exercise. This is a decision quality exercise.

Every report, dashboard, and forecast your leadership team sees is only as reliable as the data behind it. If your close dates are aspirational instead of grounded, your forecast is fiction. If dead deals are still sitting in your pipeline, your coverage ratio is inflated. If stages don’t reflect real buyer progress, your conversion metrics are meaningless. And if dollar amounts haven’t been updated since discovery, you’re planning around numbers that don’t exist.

I also want to stress that it’s not enough for you to understand this alone. Your team needs to get it too. If you’re the only one who cares about CRM hygiene, you become the manager in the memes. The goal is to help your team understand why clean data matters so they’re bought in, not just compliant. In fact, strong AE teams want their pipelines to be clean. More on this in a sec. 👀

First, let’s talk about the most common places things go sideways.

🚩 5 Common CRM Hygiene Problems

1. Zombie Deals

What to look out for:

Deals that haven’t had meaningful engagement in 30+ days with no concrete next step on the books. The prospect went dark, but the deal is still sitting in pipeline “just in case.”

What it costs you:

Zombie deals inflate your pipeline and give everyone a false sense of coverage. When you’re calculating whether your team has enough opportunity to hit the number, these deals are padding the math. That can delay important conversations about pipeline generation until it’s too late.

How to fix it:

Set a rule for your team: if there’s no scheduled next step and no meaningful two-way engagement in 30 days (or whatever threshold makes sense for your sales motion), it gets Closed-Lost. It’s not gone forever. They can always reopen it if the prospect resurfaces, but it shouldn’t be counted as live pipeline.

2. Close Dates That Keep Sliding

What to look out for:

A deal that was supposed to close last month, then this month, now next month…but nothing has materially changed. The date is just sliding forward because the AE hopes it’ll happen eventually.

What it costs you:

This is one of the fastest ways to destroy forecast accuracy. If close dates aren’t grounded in something real (a verbal commitment, a defined procurement timeline, or an actual event driving urgency), your forecast is just a collection of best guesses. It also makes it very difficult to diagnose whether you have a closing problem or a timing problem.

How to fix it:

Close dates should be backed by buyer-confirmed information. If the date moves, the AE should document why it moved and what new information informed the change. If it’s moved more than twice with no new intel? That’s a coaching conversation.

💡 Pro-Tip: During pipeline reviews, ask: “What did the buyer say or do that gives you confidence in this date?” If the answer is vague or based on assumptions, the date probably isn’t real.

3. Stages That Don’t Mean Anything

What to look out for:

A deal sitting in “Contract Negotiation” when no negotiation is actually happening, a deal in “Trial” when the prospect hasn’t logged in once, or something similar. Stages should reflect real, verifiable buyer actions, not where the AE thinks the deal is.

What it costs you:

When stages are loose, your entire conversion funnel becomes unreliable. As I talked about in my pipeline analysis post, stage-to-stage conversion is one of the best diagnostic tools you have as a leader. But if “Demo → Trial” really means “Demo → We Sent a Follow-Up Email,” your data is going to mislead you.

How to fix it:

Define clear, objective entry (and exit) criteria for each stage and make sure your team knows them. What must be true for a deal to move from one stage to the next? Write it down, review it during onboarding, and reinforce it in pipeline reviews.

4. Missing or Vague Notes

What to look out for:

Notes that say “Good call” or “Touching base next week”...or worse, no notes at all. If you can’t read a deal’s notes and understand where things stand without calling the AE, you have a problem.

What it costs you:

This might seem minor, but it compounds fast. Poor notes mean less context for coaching conversations, harder handoffs if a rep leaves, and weaker re-engagement when you try to revive a deal months later. It also makes it nearly impossible for you as a leader to prepare for pipeline reviews efficiently.

How to fix it:

Set a minimum standard: every note should capture what was discussed, what the buyer’s concerns are, what the next step is, and when it’s happening.

• Bad note: “Good call. They’re interested. Following up next week.”

• Good note: “Met with VP of Ops and Director of Finance. Main concern is integration with their existing ERP. Asked us to send a one-pager on implementation timeline. Next step: follow-up call Thursday 3/20 to walk through the technical requirements with their IT lead.”

💡 Pro-Tip: If your AEs are in back-to-back meetings and are struggling to keep up with notes, encourage them to log quick bullet points right after each call, even if it’s rough. A messy note written in the moment is 10x more valuable than a polished note that never gets written. That said, these days, with tools like Gong and Chorus that record calls and auto-generate summaries, the bar for having some form of notes has never been lower. Between quick manual bullet points and AI-generated recaps, there’s really no reason a deal should be sitting in your CRM with zero context in 2026. If it is, that’s a habit problem, not a time problem.

5. Sloppy Closed-Lost Hygiene

What to look out for:

Reps picking whatever Closed-Lost reason gets them through the dropdown fastest, or closing deals without any supporting notes.

What it costs you:

Closed-Lost reasons are a gold mine for understanding your business. They tell you whether you have a pricing problem, a product gap, a competitive positioning issue, or a qualification problem upstream. If the data is sloppy, you lose that entire feedback loop, and you’re flying blind on decisions that should be informed by pattern recognition.

How to fix it:

Require a specific Closed-Lost reason and detailed notes before a deal can be closed. As I’ve shared previously, I personally prefer having this process flow through the manager so there’s a built-in check. It reinforces learning, protects data quality, and makes sure deals aren’t being closed prematurely.

🔧 Building CRM Discipline Into Your Rhythm

So now that you know what to watch for…how do you actually keep things clean without becoming the CRM nag I mentioned earlier? 😭

Here’s what’s worked for us at SupplyPike:

• Use pipeline reviews as your checkpoint. If you’re running pipeline reviews regularly (and you should be), CRM hygiene is a natural byproduct. Every time you review a deal, you’re validating stages, close dates, amounts, and next steps. This is the easiest, most low-friction way to keep things clean.

• Set clear expectations up front. Your team should know exactly what “good” looks like in the CRM. It’s your responsibility to create guidelines and definitions around what each stage means, what’s required before a deal moves, how quickly notes should be updated, etc. Don’t assume people know this. Clarity eliminates ambiguity, and ambiguity is where bad habits grow.

• Make it part of the culture, not a punishment. The fastest way to lose your team is to make CRM updates feel like a gotcha. Frame it as ownership. The best AEs I’ve worked with want a clean pipeline because it helps them sell better. When your CRM is accurate, you can actually see where you’re strong, where you’re stuck, and where you need help. That’s empowering, not administrative. In fact, a clean pipeline is what allows my managers to quickly spot which AEs have gaps in their deal allocation (assuming the rest of their CRM data is accurate) and prioritize helping them build additional pipeline before it becomes an end-of-month or quarter fire drill.

• Do a quarterly scrub. Even with great weekly habits, things accumulate. Set aside time once a quarter to do a deeper pass. Think of it like a tune-up. 🚗 Your weekly reviews keep things running; your quarterly scrub catches whatever slipped through. If you’ve never done one before, here’s what I’d look for:

  • Stale deals: Any opportunity that hasn’t had meaningful activity in 60+ days. If there’s no next step and no recent engagement, close it out.

  • Close dates in the past: Deals with close dates that have already passed and haven’t been updated. These should be 101 for your AEs. 😮‍💨

  • Stage mismatches: Deals where the stage doesn’t match what’s actually happening. If a deal is in “Contract Negotiation” but no contract has been sent, update it to reflect where the deal truly is.

  • Dollar amounts that haven’t been updated: Deal values should reflect the most current information from the buyer, not the rough estimate from the first discovery call. Make sure these are being revisited as deals progress.

  • Contacts and decision-makers: Confirm that the right people are attached to each deal and that titles and roles are up to date. This is especially important for multi-threaded deals where multiple stakeholders are involved.

  • Closed-Lost deals without reasons or notes: Every Closed-Lost deal should have a clear reason and supporting notes. Go back and fill in any gaps. I’ve waxed poetic on this - this data is what helps you spot patterns and make better decisions down the road.

  • Duplicate records: Look for duplicate accounts or contacts that have crept in over time. Clean these up to avoid confusion and keep your reporting accurate.

💡 Pro-Tip: Most CRMs have built-in notifications, workflow rules, or flags that can help automate a lot of this. For example, you can set up alerts for deals that haven’t been updated in 30+ days, close dates that have passed, or Closed-Lost deals missing a reason. Take the time to configure these. It won’t catch everything, but it takes a lot of the manual legwork out of staying on top of data quality.

If you have a RevOps team, they can be an incredible partner for this. They can run reports ahead of time, flag anomalies, and help automate some of the cleanup so your managers and AEs aren’t doing it all manually. If you don’t have a RevOps team yet, that is totally normal at the early stage! I actually talk about when to think about adding this role in Part 3 of our GTM Planning series. In the meantime, a simple quarterly calendar reminder and a shared checklist like the one above will get you pretty far.

📈 Final Thoughts

I know CRM hygiene isn’t the sexiest topic in Sales leadership. Nobody got into this job because they were passionate about data entry (okay, maybe some of us did 🤓). But here’s the reality: the quality of your CRM directly determines the quality of your decisions. And your decisions about forecasting, hiring, territory planning, and coaching are what ultimately determine whether your team hits the number.

So, take the time to get this right. 💪🏼 Build the habits, set the expectations, and get your team genuinely bought in, not just going through the motions.

Next week, we're staying in the operating system lane. I'll be walking through how to build pricing and discounting guidelines for your sales team: what guardrails to set, how much flexibility to give your AEs, and how to make sure your deals don't turn into a free-for-all that haunts your CS team post-sale. If you've ever had an AE promise a creative discount that made you cringe, this one's for you. 👀

Till then, keep it clean, friends! 🧹
Stacy

📚 Stacy’s Book Challenge

This year’s goal is…81. 1 more than last year. 😮‍💨 Follow along as I try to get there.

As of this post, I have read 15 books. I finished Call My By Your Name and The Johnson Four this week. I ended up coming around on CMBYN (the story is just too good), and enjoyed The Johnson Four more than I thought I would! I didn’t realize it’s a ghost story (not a spoiler) because apparently I can’t read covers very well lol.

I’m currently reading:

• All Quiet on the Western Front - Err…yeah…I will finally get back to this this week

• Lonesome Dove - same as above 😬

• Heated Rivalry - I finally caved and watched the show - it’s so sweet! I had to read the book version that inspired it, though the show is honestly VERY faithful to the book, so I’m not really reading anything new. Still a fun (and very spicy) read! 🥵

Follow me on GoodReads! 🤓

In the early days, this question is usually asked and answered pretty informally. The CEO might turn to you in a leadership meeting or send a late-night Slack, and you give your best guess based on the deals you’re seeing.

As the business grows, forecasting becomes increasingly important because more parts of the company rely on it. Finance needs visibility for planning. Product wants to understand which customer segments are actually converting. Leadership needs a clearer picture to make decisions about hiring, spending, and priorities.

At that point, the forecast stops being just a sales exercise and becomes something the entire company is paying attention to. 👀

When that shift happens, it’s usually a good signal that it’s time to think about how you formalize sharing your forecast with a broader group. There isn’t one “right” way to do this, but over time, we’ve found a simple framework that can help structure that conversation.

🥽 Before We Dive In

It’s worth saying up front that forecasting will never be perfect. 🥲 Even very experienced teams get it wrong sometimes. Deals slip, buyers unexpectedly go quiet, legal takes longer than expected, or a deal that felt certain suddenly disappears. That’s just part of running a sales organization.

The goal of forecasting isn’t to remove all uncertainty. Rather, it’s to build a system that helps the company see what’s likely coming and get a little more accurate over time, so you can make better decisions along the way.

Let’s get into it!

🤝 The Setup

In the early days, I strongly recommend running forecast meetings weekly, or at least biweekly. We still run ours weekly today.

Sales cycles move quickly, and the cost of being surprised late in the month or quarter is high. A weekly rhythm allows you to refine your understanding of where things stand and catch problems early enough to actually do something about them.

💡 Pro-Tip: It’s important to distinguish this meeting from pipeline reviews. Pipeline reviews are where you go deep with AEs on individual deals. Forecast meetings are where those individual calls roll up into a company-level view of the business.

A few practical guidelines that have worked well for us:

Cadence

• As noted, weekly is ideal in the early days.

• Consistency matters more than perfection. The goal is to build a rhythm where leadership regularly understands where revenue stands. In early-stage companies, especially, it can be surprisingly easy for teams to keep their heads down and say, “I’m focusing on my own thing. I don’t really know how the company is doing.” That’s a dangerous place to be.

Who Should Attend

• Sales leadership

• Finance leadership

• Company leadership (CEO, COO, etc.)

Depending on the size of your business, you may also find it useful to include:

• Marketing or demand generation leaders

• RevOps

• Product leadership (if customer trends are relevant)

As the company grows, the forecast becomes a signal that multiple teams rely on. Having shared visibility into the numbers helps everyone operate with the same understanding of the business.

📓 What to Report

The starting point for any forecast meeting should be what you expect to close this month.

If you’re effectively running your pipeline reviews 😉, your AEs should already be calling their numbers. As the Sales leader, your job is to roll those calls up and form your own point of view based on what you’re seeing across the pipeline.

This becomes your forecast for the month: the number you believe the business will realistically close if things continue progressing as expected.

At SupplyPike, we frame this in three scenarios:

• Likely Case: Your realistic expectation

  • This is what leadership should use for planning and should very closely align with the roll-up of your reps’ calls.

  • If there’s a big discrepancy between what your reps are calling and what you’re comfortable committing to, it’s worth asking whether those “calls” are truly calls. 👀

• Worst Case: What happens if several deals slip or fall through

  • This helps the team understand downside risk.

  • If you’re seeing broader trends (legal taking longer to provide counter redlines, holidays approaching, buyers slowing down, etc.), it’s worth planning for those possible outcomes.

• Best case: What happens if everything breaks your way (sending you good juju for this!!! ✨)

  • This usually includes deals that feel possible but are not quite ready to be called yet.

  • This scenario helps leadership understand what upside could look like if momentum is strong. Just be careful not to treat this number as something the company should plan around (a very easy trap to fall into!).

As the company grows, you’ll also want to start looking beyond the current month. Most companies eventually forecast through the current quarter.

For example, if you’re in Q2, you might think about it like this:

• April: You should have a pretty strong understanding of what will close, and that confidence should increase as the month progresses.

• May: You likely have some visibility, but there’s still room for movement. You may use a combination of rep calls and some pipeline modeling (more to come here).

• June: You may rely heavily (or even solely) on pipeline modeling to get an idea of what forecasted $ could look like.

💡 Pro-Tip: There’s also some nuance in forecasting depending on your sales motion. In SMB-heavy businesses, visibility drops off quickly as you move out in time because deals can appear and close relatively fast. In enterprise sales, you often have clearer visibility into the quarter because deals are larger and move through longer, more structured buying processes.

🧮 Quick Detour: What Exactly Is…Pipeline Modeling?

One of the simplest ways to start modeling pipeline is through weighted forecasts. A weighted forecast applies probabilities to deals based on where they are in the sales cycle. For example:

• Demo stage = Estimated ARR × 10% probability

• Trial stage = Estimated ARR × 50% probability

• Contract Negotiation stage = Estimated ARR × 75% probability

It may look a little something like this…

🔮 In Sum

Below is a simple example of what a forecast snapshot could look like in a leadership meeting…

Some quick takeaways you can get from this example:

• The quarter is trending slightly up week-over-week. The Q2 forecast increased by $4K compared to last week. Most of that improvement is coming from May (+$13K), partially offset by a drop in June (-$14K).

• May and June are the primary areas of risk. While April is currently forecasted above goal by $7K, May and June are both trending below goal, with June showing the largest gap (-$26K). That suggests the team should focus attention on late-stage deals expected to close in those months.

• June slipped week-over-week. This could indicate deals pushing later in the quarter or pipeline that wasn’t as mature as expected.

• YOY performance is still trending positively overall. Even with the current gap to goal, the Q2 forecast of $235K is slightly ahead of last year’s actuals of $230K.

Why Compare Against Your Previous Forecast?

Including the previous forecast helps answer an important question: what changed?

Forecasting isn’t just about where the numbers stand today. It’s about how your expectations are evolving. If the forecast moves significantly week to week, seeing those changes side-by-side helps the team quickly identify what’s driving movement in the business instead of treating every forecast as a completely new snapshot.

Why Include Last Year (If You Have It)?

Looking at the same period from the previous year can also provide useful context, especially if your business has any seasonality.

Some companies naturally see slower months during the summer or around major holidays. Others see stronger buying activity at the end of fiscal years. Without historical context, it’s easy to misinterpret normal seasonal patterns as something going wrong.

When available, last year’s data helps anchor the conversation and provide perspective on what “normal” might look like.

A Quick Note on Pipeline Coverage

One additional lens that can be helpful when reviewing your forecast is pipeline coverage.

While forecasts rely on judgment (what reps believe will close and how deals are progressing), pipeline coverage asks a simpler question: Does the math support the story?

For example, say (as shown above) that your May goal is $88K, and you have $120K in pipeline with a forecast of $78K. If your forecast consists of rep calls and a weighted pipeline, you are assuming a conversion rate of roughly 65%. That sounds great on paper, but is (sadly) unlikely. 😩 Assuming your reps’ calls are solid for the month, the more likely takeaway is that you probably need more pipeline. The math is simply telling you that you don’t have enough opportunities entering the funnel to comfortably support the number.

Many SaaS companies aim for around 3x coverage, though the right number depends on your sales motion.

🤔 Now What?

Once the numbers are on the table, the next question becomes: what do you do with them?

Start with the current month. Ideally, your Likely Case should already put you reasonably close to goal. If it doesn’t, that’s a signal worth digging into early rather than waiting until the end of the month.

A few questions that are helpful to explore:

• Are there late-stage deals that need additional support from leadership/other teams to get across the finish line?

• Are there opportunities with Close Dates in the next month that can potentially be pulled in if needed?

Next, look at future months in the quarter.

If the next few months’ forecasts are trending below goal, the conversation usually shifts toward pipeline creation. Do you have enough opportunities entering the funnel? Are demo bookings trending where they need to be? Are upcoming events, marketing campaigns, or outbound efforts expected to generate additional pipeline?

This is also where forecasting becomes a useful alignment point across teams. Sales, marketing, and leadership can look at the same numbers and decide how to deploy resources.

• If the current month/quarter is already in good shape, you may invest in longer-term programs, like brand campaigns or larger events (where pay-off takes some time).

• If there’s a forecasted gap in revenue right now or in the near future, the focus may shift to faster pipeline sources, like paid ads, outbound pushes, or near-term events.

🙂‍↕️ Final Thoughts

The goal of forecasting isn’t to be right every time. If one of you is able to figure out how to get 100% accuracy with yours…give me a call. I’ve got some investors I can line up for you. 😂 These meetings exist to help your company understand where things stand early enough to act on them. When forecast meetings work well, leadership has visibility into the quarter, teams understand where risk exists, and decisions get made sooner rather than later. A win for everyone.

Next week, we’ll talk about something that powers all of this: CRM hygiene. And boy oh boy does my RevOps team have strong feelings about this. 😮‍💨 Even the best forecasting process falls apart if the underlying data isn’t trustworthy, so stay tuned for some good tips on keeping your house clean!

In the meantime, happy forecasting! 🔭
Stacy

📚 Stacy’s Book Challenge

This year’s goal is…81. 1 more than last year. 😮‍💨 Follow along as I try to get there.

As of this post, I have read 13 books. I finished The Wedding People, Interior Chinatown, and Twice. The first two got 5 ⭐️ reviews from me! So much thought-provoking storytelling. Twice was very meh - go watch About Time instead.

I’m currently reading:

• Call Me By Your Name - I won’t lie…I’m not super loving it - like we get it, you’re in love lol

• All Quiet on the Western Front - I got distracted with some other books (clearly)…gotta pick this one back up this week

• Lonesome Dove - same as above 😬

• The Johnson Four - I just started this one! It’s been very interesting so far

Follow me on GoodReads! 🤓

If you zoom out, all of it ultimately points to the same thing:

1. Numbers matter

2. They matter even more when the person responsible for them understands how to influence them

That’s where Sales leadership can get tricky. Because early on, your job is to help reps influence the number. You inspect deals, tighten positioning, fix forecasts, and step in when something feels shaky. But if you stay there too long, you risk becoming the operator of everyone else’s business instead of the coach who builds operators.

Today’s article tackles how to coach your reps from simply knowing their book of business to truly owning it, and ultimately learning to drive it themselves. 🚗💨

🤓 From Awareness to Ownership

🧠 Knowing Their Business

At the earliest stage of AE development, the bar is clarity. At the very least, reps need to know their numbers. They should be able to tell you their pipeline coverage, their commit, their quota, and their exact gap to goal. That sounds obvious, but it’s amazing how often early reps operate on feelings. In the early days of SupplyPike, we had AEs who didn’t know what their quota was, let alone how far away they were from it. 💀

At this stage, AEs are primarily reporting what’s happening. If a deal slips, it’s unfortunate. If pipeline is light, it’s circumstantial or out of their control. They can answer factual questions, but might struggle with causality. Said another way, they’re able to describe outcomes, but not the drivers behind them.

How to Spot This Stage

You’ll hear things like:

• “I think I’m in decent shape.”

• “This deal just needs a little nudge.”

• “I’m waiting to hear back.”

• “Pipeline’s been weird lately.”

At This Stage, Your Job Is To:

• Create clarity.
  Early reps don’t thrive in ambiguity. Make sure they always know their four key numbers (or any other KPIs you deem important): quota, current attainment, pipeline coverage, and commit. Ask questions like, “What’s your exact gap to goal right now?” If they hesitate, that’s a signal. Help them build the habit of calculating their numbers themselves before every pipeline review. You want them to walk into meetings already aware of their scoreboard, not discovering it in real time with you.

• Teach the language of the business.
  Words like “coverage”, “conversion”, “average deal size”, and “sales cycle” get thrown around a lot. Don’t assume understanding. Sit down with your reps and walk through a real example from their book. If they have $200K in pipe against a $50K monthly quota, what does that actually mean? If their sales cycle is 45 days, what needs to be created today to support next month? Tie every metric to behavior, and help them to understand what levers they have to hit their goals (more on this later).

• Model inspection.
  When you review a deal, narrate your thinking! 💬 What feels obvious to you may be brand new for your AEs. Say things like, “I’m nervous here because we don’t have the economic buyer engaged,” or “This feels risky because next steps haven’t been aligned on.” Early reps often don’t know what to look for. By explaining your reasoning out loud, you’re teaching them how to evaluate deals independently. Over time, you want them to start saying those same things before you do.

• Build preparation habits.
  Set the expectation that pipeline reviews are not status updates. They are working sessions. Reps should already know which deals are at risk, which ones are stalled, and what their plan is. If they consistently show up unprepared, don’t just fill the gap for them - push them to provide answers. It may feel inefficient (and painful 😮‍💨) at first, but you’re helping them to build muscle memory.

🔑 Owning Their Business

As reps mature, the conversation should shift from “What’s happening?” to “Why is it happening?” They begin to understand the mechanics underneath their results. They know their overall close rate and their stage-to-stage conversion. They can calculate how many new opportunities they need to create each month based on their historical averages. They can articulate where their deals tend to stall and why. When they’re behind, they don’t just say they’re off pace; they can point to the driver.

How to Spot This Stage

You’ll hear:

• “My Trial → Contract conversion has dipped this quarter.”

• “I’m not setting clear success criteria early enough.”

• “If this slips, I need two more demos this month to stay on track.”

• “I’m strong in discovery, but negotiation is where I need some support.”

At This Stage, Your Job Is To:

• Shift from telling to questioning.
  When a rep says they’re behind, don’t jump straight to the fix. Instead, ask, “What do you think is driving that?” For example, if their Demo → Trial conversion dropped, ask them what they think changed that might have led to the decrease. The goal is to train diagnostic reflexes. You want them thinking in cause and effect without you prompting every time.

• Make them run the math themselves.
  If their pipeline feels light, don’t calculate the gap for them. Have them walk through it. “Your quota is $75K, and you’ve called $40K. Your close rate is 25%. Do you have enough pipeline to stay on track? If not, what levers can you influence to hit goal?” Once they see the equation clearly, they begin to understand which inputs they can change to impact the outcome.

• Coach trends, not just transactions.
  When you review deals, zoom out. Say you are reviewing Closed-Lost opportunities. You can ask questions like, “Over your last 8 deals, what pattern do you see?” If the answer is always “bad timing,” push further. Is it really timing, or is urgency not being created early enough? Are they multi-threading? Are they qualifying budget explicitly? Help them get a better understanding of their patterns so they can be more aware of how they run deals and make adjustments accordingly.

• Normalize accountability without drama.
  Owning the numbers means seeing the gaps clearly. Some reps interpret that as pressure or criticism. Your job is to frame it differently and shift the mindset from blame → control. Keep your tone analytical instead of emotional, so your reps learn that being behind is not a crisis. It’s simply a data point that requires a plan.

🚗 Driving Their Business

When a rep is truly driving their business, they don’t just understand what’s happening; they can anticipate it. They’re not surprised by their numbers. If conversion dips, they’re already testing a change. If next quarter looks thin, they’ve already adjusted their outreach activity mix. They don’t escalate because they’re stuck, but rather ask for input because they’re refining their strategy.

Reps that drive their business treat their territory or book like a small company they are responsible for growing. They think about risk, balance, and long-term health, not just this week’s demo.

How to Spot This Stage

You’ll hear:

• “If I don’t build $X in new pipeline this month, Q3 will be tight.”

• “I’m testing a new disco structure to improve conversion.”

• “I don’t need help on this deal, but I’d love feedback on how I’m approaching pricing.”

• “My average deal size is trending lower, so I need to prioritize larger accounts to stay on pace.”

At This Stage, Your Job Is To:

• Elevate the conversation from deals to strategy.
  At this stage, if you’re still spending all your time asking, “Is this going to close?” you’re under-utilizing your experienced reps. Start zooming out. How are they allocating their time? Are they defaulting to the loudest deal, or the highest-leverage one? Are they protecting next quarter, or just trying to land this one? Driving reps should be thinking about the mix of their current book and long-term pipeline health.

• Stress-test their assumptions.
  When they present a forecast, challenge it constructively. “What’s the biggest risk in this plan?” “What would cause this to slip?” “If this deal dies tomorrow, what’s your backup?” This isn’t about being skeptical of their numbers. It’s about helping them to sharpen their foresight. The best reps start asking themselves these questions before you ever do.

• Give autonomy, but stay strategically available.
  This one is hard, especially if you’re used to being in the trenches. You’ll see something you’d handle differently. Let it go (unless it’s fatal).

  

  Resist the urge to insert yourself into every deal. If they ask for help, clarify what kind. “Do you need tactical support, or do you want perspective?” High-level reps don’t need you rewriting their emails. They need you expanding their thinking and constructively challenging their approaches.

• Prepare them for what’s next.
  If your AEs are truly driving their business, start treating them like future leaders. 🏆 Have them mentor a newer rep or ask them to share insights in a team meeting. Let them see how you think about hiring or capacity decisions - many are curious about how things work “behind the scenes”. Several of my strongest reps eventually stepped into leadership roles. That didn’t just happen because they hit quota - it happened because they learned to think beyond their own book.

🤺 Coaching the Shift

This progression doesn’t happen by accident. It happens because you deliberately change how you lead. Here are some things you can put into practice today.

Make pipeline reviews an AE-led meeting.

If you’re leading pipeline every week, you’re still running your AEs’ business. 😭 Shift the burden to them. We covered what this should look like in-depth a few weeks ago, so I won’t wax poetic here. Just keep in mind that AEs should be able to give you clear paths to closing their deals and hitting their monthly goal. If they can’t, they don’t know their business yet.

Build a quarterly gut-check.

Weekly pipeline reviews are important, but tactical. They focus on what needs to close now. If you have the data, create a quarterly performance snapshot for each AE, including metrics that drive outcomes like:

• Overall conversion rate

• Conversion rate by stage

• Average deal size

• Sales cycle length

• Top Closed-Lost reasons

Review it together once a quarter, and start with one question: What stands out to you? Discuss insights, learnings, and what they should focus on.

Where possible, build live dashboards in your CRM that surface these metrics automatically, instead of relying on ad hoc spreadsheets. When reps can see their KPIs regularly in one place, the data becomes part of their operating rhythm, not just something that gets reviewed when something goes wrong.

Run the math together, then make them run it alone.

Instead of telling your reps, “You need more pipeline,” walk through the equation. Have them calculate how many new qualified demos they need per month to sustain their number. Then ask what happens if conversion rate dips or if their average deal size shrinks.

Once they see the equation clearly, the number stops feeling intimidating and starts feeling within their control. They can see which lever matters most in the moment:

• Pipeline

• Conversion rate

• Average deal size

• Cycle time

💡Pro-Tip: There’s a lot of nuance to this section - not every rep can meaningfully influence every lever. For example, an SMB rep probably cannot materially increase average deal size (pricing and packaging are largely fixed), but they can optimize for cycle time and pipeline volume. Conversely, an Enterprise rep may not be able to dramatically increase top-of-funnel volume (this segment often has a more limited market), but they can maximize conversion by multi-threading within existing opportunities. The goal is to help your reps identify which lever they can realistically pull right now, and then act on it.

Coach to losses, not just live deals.

One of the most powerful tools I’ve found is carving out intentional time to review losses with your reps. At SupplyPike, we use a “blameless post-mortem” mindset (not just in Sales, but across the company, and it’s awesome). The goal isn’t to point fingers, it’s to learn together. Pull the last quarter of Closed-Lost deals and ask:

• Where did these die in the funnel?

• What was the stated reason vs. the likely real reason?

• What were the top reasons these deals were lost?

• Was multi-threading present?

• Was urgency clearly defined?

Patterns live in losses. If five of the last eight deals died in Demo → Trial, that’s not necessarily “bad luck.” It’s likely a signal to dig deeper into discovery and urgency-building. When reps start reviewing losses this way, they learn to stop treating deals as isolated events and start seeing their pipeline as a system with inputs and outputs that they can control (are you noticing a pattern here? 👀).

Make them propose the plan before you improve it.

When a rep says, “My pipeline is light,” or “Deals keep slipping,” the instinct for most managers is to jump straight into solution mode. You’ve seen this before. You probably know the likely fix. But if you immediately hand them the playbook, you’re solving the short-term issue at the expense of long-term development.

Instead, ask them what they think needs to change. The first pass won’t always be perfect, but that’s not the point. The point is that they’re building the habit of diagnosing before escalating. Once they propose a plan, you can refine it together. Instead of “What should I do?” the goal is to get to, “Here’s what I’m seeing, and here’s what I’m going to try.”

🪤 Coaching Traps That Undermine Ownership

On paper, the progression from knowing to owning to driving makes perfect sense. In reality, it can be way harder to put into practice, because leadership is busy (you’re trying to build a company, for Pete’s sake!), the number is real, and everyone is trying to land the month. 🥴

Here are a few surprisingly easy traps to fall into (and what to try to avoid).

The Manager Ego Trap

If you’re strong or experienced at sales, it is incredibly tempting to step in. I know, I’ve done it.

You’re on a call, and you hear the discovery question that could’ve gone deeper. You read the follow-up email and immediately start rewriting it in your head. You see the pricing conversation and think, “I would’ve said that differently.”

And most of the time, you’re probably right.

But every time you step in and “fix” the deal, you reinforce a dynamic, even if you don’t mean to. You teach your reps that when it gets hard, you’ll handle it. Over time, they stop pushing their own thinking because they know you’ll catch it.

There’s a big difference between modeling excellence and becoming the closer. If your team can’t consistently win without you, you’re still running their business. 🙅🏻‍♀️

The Comfort of Activity

This one can be sneaky.

Some reps are incredibly busy. Their calendars are packed with demos, calls, and follow-up tasks. While activity can be a great leading indicator of success, it’s far more important to understand if that activity is converting and if it’s effective. Stage conversion numbers, pipeline math, and forecast hygiene don’t reward effort. They reward outcomes.

When you start shifting the conversation from “How hard are you working?” to “Is it working?” it can feel uncomfortable, even when it’s not meant to be. It’s still important to press on. The goal is create a culture that celebrates progress, not just movement.

Fear of Accountability

Ownership requires visibility, and that can feel uncomfortable at first.

When a rep really understands the math behind their number, like how many qualified demos they need, what their close rate actually supports, and what coverage has to look like, the gap stops being fuzzy and gives them less room for “I think I’ll be okay”. This can feel uncomfortable because it feels like their weaknesses are being exposed. Your job is to make that honesty feel safe.

Be clear that this level of clarity isn’t meant to embarrass anyone. It’s meant to help them decide what to do next. When numbers feel like information they can act on, they lean in rather than shy away. If you get this part right, you don’t have to force accountability. It shows up on its own. 🙏

😅 When Coaching Isn’t the Problem

One quick note: everything above assumes your rep actually wants to improve. Most do. Unfortunately, sometimes the issue isn’t clarity or coaching style. It’s simply performance and attitude. 😮‍💨

You’ll know coaching may not be the lever when:

• The same feedback is given repeatedly, and nothing changes

• They can articulate the math, but don’t adjust behavior

• Every gap is not their fault - it’s pricing, marketing, the territory, the economy…you name it

• There’s no visible effort to experiment, test, or improve

• Conversations about numbers consistently turn defensive rather than curious

Coachable reps might struggle or miss or get frustrated, but they show up, engage, try, and iterate. This framework works when someone is willing to look at their numbers honestly and take ownership. If they’re not willing to do that, the conversation shifts from coaching to accountability. And that’s a different article for a different day. 😇

🪩 Closing Thoughts

This entire month has really been about one thing: helping your team build confidence through clarity. Meeting cadence, pipeline, and conversion rates matter. But none of it works the way it should unless your reps actually understand how their business functions, and believe they can influence it.

I will die on this hill: if you want reps truly bought in, they have to understand their business. Not just their quota, but the math behind it. They need to see how pipeline turns into revenue, and they need to believe the number is fair, achievable, and within their control.

The more they understand the system, the more confident they become. The more confident they become, the more ownership they take. The more ownership they take, the more consistent the results. 💪

Next month, we’ll zoom out from individual ownership and talk about something equally important: the systems behind the number. 🤖 We’ll spend some time talking about creating and reporting on company forecasts, why CRM hygiene matters, early RevOps decisions, and talking through philosophies on things like segmentation and stage definitions. Excited to nerd out with y’all in March!

Go sell something! 💰
Stacy

P.S. Before you go, I wanted to share a quick personal note. I’m helping support the Leukemia & Lymphoma Society right now. The funds raised go toward research that’s literally saving lives, but also toward practical support for families navigating blood cancer, including things like helping parents take time off work to be with their kids during treatment. If you’re in a position to give, even a small amount makes a difference. You can donate here. I’m incredibly grateful for the support. 💛

📚 Stacy’s Book Challenge

This year’s goal is…81. 1 more than last year. 😮‍💨 Follow along as I try to get there.

As of this post, I have read 10 books. Woohoo! I finished Odyssey and Anatomy of an Alibi earlier this week. The former was great (if you enjoy mythology, I highly recommend this series by Stephen Fry - it’s so accessible!), and the latter was…fine. 😂

I’m currently reading:

• Call Me By Your Name - Ugh the movie was SO GOOD - thought I’d read this one for all the feels

• The Wedding People - I’ll be honest…I didn’t expect to enjoy this book as much as I have. It’s light, but still with some really great messages. I’m about 80% through, and recommend it so far!

• All Quiet on the Western Front - another one I wasn’t expecting to enjoy this much - the writing is sharp (even if the story is depressing)

• Lonesome Dove - I’m realizing I’ve started too many books this week…anyway - I’m only on page 10 here…but it is another 700+ page book 😭

Follow me on GoodReads! 🤓

This week, I want to zoom out a bit. As we learned, pipeline reviews aren’t just about this month’s number. When done well, they can be one of the best diagnostic tools you have as a leader. When you review deals consistently and with structure, patterns start to emerge. Certain reps get stuck at the same stage, or certain deals tend to stall at the same point. Trends like that can tell you where your AEs (or your sales motion) are strong…and where they need support.

So today, we’re going to talk about how to use stage-by-stage conversion to coach more intentionally, so you stop asking, “Why aren’t we closing more?” and start asking, “Where is this actually breaking?” 👀

✍🏼 A Few Quick Assumptions

Before we get into it, I wanted to level set on a few assumptions.

First, most startups have some version of:

Initial Demo → Trial (or POC) → Contract Negotiation → Closed-Won / Closed-Lost

The stage names might be different for your org, or you may have additional (or fewer) steps. I’m going to keep it general to the stages above so you can apply this post to your business as needed.

Secondly, this post will make the most impact if your leads are reasonably qualified and aligned to your ideal customer profile (ICP). If your AEs are consistently taking demos with companies that don’t have budget, don’t feel real pain, don’t match your ICP, or were never serious buyers to begin with, your stage conversion analysis is going to tell you more about your top-of-funnel than it will about rep skill.

For example, you may see a weak Demo → Trial conversion and think you have a discovery problem, when in reality, you may have a targeting or qualification problem. Stage-by-stage analysis is a powerful coaching tool, but only once you’re confident that the opportunities entering the system are directionally right.

For this conversation, we’re assuming all your leads are super-duper qualified and ready to sign. 😜

1️⃣ Demo → Trial

What this stage represents:

This is the moment where your AE is representing your business in a real way for the first time and truly earning the right to move the deal forward.

They’re running discovery, yes, but more importantly, they’re figuring out whether there’s actually something here worth solving. They’re surfacing real pain, connecting it to your solution, and helping the prospect start to believe this could actually make a difference. They’re also creating urgency by helping the buyer see why this matters now, not six months from now.

If conversion is low, diagnose:

• Discovery is too shallow (surface pain vs. quantified impact).
  Listen for whether the AE is uncovering real business impact or just nodding along to general frustrations. “Yeah, reporting is annoying” is not the same as “This costs us 15 hours a week and delays executive visibility.” If the AE can’t articulate the financial, time, or operational impact, the buyer won’t feel urgency either.

• The demo turns into a feature tour instead of a pain conversation.
  You’ll hear the AE walking through slide after slide or clicking through every tab just to show it. The product is being presented comprehensively, but not strategically. Instead of saying, “Based on what you told me about X, let me show you how we solve that,” they’re defaulting to a scripted walkthrough. When that happens, the buyer stays in observer mode instead of leaning in. It often feels like the AE is simply checking things off instead of tailoring the call.

• Urgency isn’t being established (“This is interesting” vs. “We need this.”).
  Pay attention to the emotional tone of the call. Is the buyer reacting with curiosity or with concern? If the conversation never transitions to consequences (what happens if this isn’t fixed?), then the deal can slide into “circle back next quarter” territory.

• No concrete next step is locked in before the call ends.
  If the demo ends with “I’ll follow up” instead of a scheduled trial kickoff (or whatever the next step is), that’s a red flag. 🚩 Strong AEs don’t let their prospects drive the sales cycle. They secure commitment in the moment. If next steps consistently feel loose, that’s usually a confidence or control issue.

How to spot it:

• A pattern of deals going Closed-Lost right after demo

• Lots of ghosting after “we’ll discuss internally”

• CRM notes heavy on features the customers liked, light on the business problem, impact, and next steps

• Buyers don’t show up for the follow-up meeting

How to coach it:

• Review call recordings together.
  Don’t just say, “That was a good call” or “You need better discovery.” Pause the recording during the first 10-15 minutes and ask: What did we actually learn here? Could we clearly explain the customer’s business problem to someone else on the team? Where did we miss an opportunity to go deeper? This one can be tough, but where you can, help the AE get comfortable sitting in silence and asking one more question (you know the age-old saying…we have two ears and one mouth, so we should be listening twice as much as we talk!). Often, the first answer is surface-level, and the second is where the real pain lives.

• Force a one-sentence pain summary.
  After the call, ask the AE: “In one sentence, what is this customer trying to fix?” If the answer sounds like marketing copy (“They want better visibility”), push further. What kind of visibility? Why does it matter? What happens without it? If they can’t say it simply and specifically, they probably didn’t anchor their discovery (or demo) tightly enough around it.

• Role-play urgency conversations.
  Many reps are comfortable explaining features but uncomfortable leaning into consequences (it’s no fun to push prospects into getting uncomfortable!). Practice it with them. Have them say out loud: “What happens if this doesn’t get solved this quarter?” or “What’s the cost of waiting?” It may feel direct at first, but urgency is created by helping the buyer articulate impact in their own words.

• Coach stronger closes on the call.
  Listen to how the demo ends. Does the AE confidently suggest the next step? Or do they default to, “I’ll send some information and follow up”? Coach them to assume forward motion: “Based on what we discussed, the next logical step would be a two-week trial focused on X. Does that make sense?” Then (and this part really matters), get it on the calendar before hanging up. Assume the yes!

2️⃣ Trial → Contract Negotiation

What this stage represents:

This is where your product has to prove itself.

The buyer has moved past “this sounds interesting” and into “does this actually work for us?” They’re interacting with the product, bringing in colleagues, and beginning to form internal opinions.

Your AE’s job here isn’t to sit back and hope the product sells itself. It’s to manage the experience by ensuring the trial is structured around the specific pain uncovered in discovery and guiding the buyer toward a clear conclusion.

Strong AEs don’t just run trials; they orchestrate them. If conversion is low here, something is breaking in how the trial is being positioned, managed, or experienced.

If conversion is low, diagnose:

• The trial is being treated as passive instead of managed.
  If the AE sets up the trial and then disappears until it’s over, that is no bueno! 🙅🏻‍♀️ Listen and look for whether there were structured check-ins, clear goals, and agreed-upon milestones. A trial without ownership quickly becomes “we tested it a bit” instead of “we validated it works.”

• There was no defined success criteria upfront.
  Before the trial started, did both sides agree on what success looks like? Or was it just “let’s try it out”? If there’s no shared definition of a win, the buyer has no clear reason to say yes at the end.

• Pain-to-product alignment breaks down.
  This is subtle but common. The buyer said they care about time savings because they’re understaffed. But during the trial, the focus shifts to customization features or reporting aesthetics. Your AE’s job is to guide the buyer back to what they originally said they wanted to solve. Quick note: That doesn’t mean the scope can’t evolve. If a real, adjacent pain surfaces that meaningfully expands the opportunity, your AE should be able to pivot. Just make sure it deepens the value story, and doesn’t end up distracting the deal!

  • 💡Pro-tip: Be very careful about promising future features.
    This is every AE’s Achilles’ heel (ask my Product team lol). The buyer asks, “Can it also do X?” and the rep says, “Not yet, but it’s on the roadmap.” Be very careful here. The moment you shift from proven value to hypothetical value, you introduce risk. If the deal now depends on something that doesn’t exist yet, you’ve weakened your position. Coach your team to anchor on what the product does today and how that solves the defined pain.

• It might just be a product issue. 😮‍💨
  If multiple reps are losing deals at this stage with similar feedback (“it didn’t quite do what we needed”), don’t automatically default to coaching. This could be a signal for your Product team. Make sure you’re passing that feedback on!

How to spot it:

• A pattern of deals going Closed-Lost right after trial

• Prospects saying “I didn’t get what I expected” or “It wasn’t what we needed”

• Low engagement during the trial period

• AEs unable to clearly explain what the customer tested and learned

How to coach it:

• Require a pre-trial success plan.
  Before kickoff, don’t just ask, “Are we ready?” Sit with the AE and ask: What pain are we solving in this trial? What outcome are we trying to prove? Who has to believe this worked in order for the deal to move forward? If the answers are vague, push for additional clarity (and maybe even a trial kick-off call with the prospect). Trials without defined success criteria can drift in scope and timing. Be clear about what the win is.

• Schedule structured check-ins.
  Open the calendar with your AEs. Ask: When is the midpoint review? When are we closing the trial out? If those meetings aren’t booked upfront, you’re hoping the buyer drives momentum, which means you’ll be lucky to close the deal a year from now. 😭 Coach AEs to treat the trial like a project plan, not a free sample. Control doesn’t have to mean you’re pressuring or rushing your prospects. Rather, you are acting like the expert to help your prospect understand where to go next. More often than not, this is the first time they’re buying a product like yours. Help them to help you!

• Drive outcome-based language.
  Listen to how AEs talk during trial follow-ups. Are they asking, “How’s it going?” or are they anchoring back to the original pain? Practice phrasing like: “You mentioned this was costing you 10 hours a week. Have we proven that we can eliminate that?” That subtle shift reminds the buyer why this matters in the first place.

• Zoom out if the pattern is consistent.
  If one rep is breaking here, coach the rep. If three reps are breaking here in similar ways, zoom out. Ask yourself: Is this onboarding friction? Is this a product gap? Is this expectation-setting? Don’t let your reps internalize what might actually be a systemic issue. Good leaders know when to coach the individual and when to escalate the pattern.

3️⃣ Contract Negotiation → Closed-Won / Closed-Lost

What this stage represents:

If you’ve reached contract review, the buyer already believes the problem is real, and has likely validated that your solution works. At this point, you’re aligning on pricing, terms, and execution. This stage is about confidence and control.

Your AE needs to reinforce value, navigate procurement dynamics, and guide the deal through internal approvals without losing momentum. When deals break here, it’s rarely because the product suddenly stopped being good. It’s usually friction around money, terms, or stakeholder alignment.

If conversion is low, diagnose:

• Pricing isn’t anchored in value.
  Listen for how the AE introduces pricing. Do they jump straight into numbers? Or do they re-ground the buyer in impact first? “It’s $40K annually” lands very differently than “We aligned that this saves your team 10 hours a week and eliminates X risk. Based on that, the investment is $40K annually.” If the AE doesn’t reconnect price to business outcomes, the number will feel big in isolation.

• The AE gets uncomfortable during negotiation.
  You’ll hear it in tone and pacing, often showing up as softer language or quick discounting. Instead of asking clarifying questions like, “We had alignment before. Help me understand what changed,” they concede to keep things moving. When reps avoid discomfort, they often trade margin for relief. The buyer may think, “If they discounted this easily, it was overpriced to begin with,” which weakens your position and limits your leverage.

• Late-stage stakeholders weren’t identified earlier.
  If legal or procurement suddenly appears as a blocker, that represents a (big) miss from earlier in the cycle. Was the signing authority clearly identified? Did the AE ask about the approval process and timeline? When new decision-makers surface late, it often means discovery didn’t go deep enough on internal dynamics.

• There’s no clear path for flexibility.
  Listen for hesitation when buyers push on terms or pricing. Does the AE know what they can and can’t negotiate? When escalation paths are unclear, reps are bottlenecked or have a tendency to overpromise. Ambiguity inside your org creates friction outside of it.

  • 💡Pro-tip: Work closely with Finance and CS on pricing guardrails.
    In the early days, some flexibility is healthy. You’re testing pricing, packaging, and service models. Once you start to see a model that feels scalable, tighten it up. If your AEs are selling like it’s the wild wild west 🤠 (custom terms here, one-off discounts there, creative service bundles everywhere), your AMs and CSMs will feel it immediately. Ask me how I know. 😮‍💨 What looks like “closing a deal” in Sales can turn into a dumpster fire post-sale. If you want you and your CS leader to stay friends, partner closely with them to understand what’s sustainable long-term, while also providing flexibility to your AEs. As a leadership team, continue to pivot when needed. But make those pivots deliberate, and not reactive side effects of late-stage negotiations.

How to spot it:

• A pattern of deals sitting in “Contract Sent” for weeks

• Last-minute discount pressure that wasn’t present earlier

• Buyers saying, “We went with a cheaper option”

• AEs expressing frustration like, “Everything was good until legal”

How to coach it:

• Re-anchor on ROI before price.
  When you’re reviewing a deal that’s entering the contract stage, sit with the AE and ask: What value have we clearly quantified? What business impact are we aligned on? If you took pricing off the table for a second, could you confidently explain why this is worth it? If the conversation with the buyer has shifted straight to numbers, slow it down. Coach the AEs to revisit the outcomes first. For example: “We aligned that this would save your team 10 hours a week. Does that still feel accurate?” Once they confirm the impact, you can transition naturally to: “Based on that, the investment to make this happen is $X annually.” Price should feel like a logical next step, not a surprise.

• Practice negotiation before it happens
  Before the contract goes out, role-play the hard part. What happens if they ask for 20% off? What if procurement says it’s outside budget? What if legal pushes back on terms? Have the AE say the words out loud. “When we aligned on the value earlier, this felt like a priority. What’s different now?” Or: “If budget weren’t the constraint, would this be the right solution for you?” I could write a whole post about negotiation (and I just might 👀).

• Map stakeholders early (and fix it in the next call if you didn’t).
  If procurement friction keeps popping up late, don’t just blame legal. Ask: When did we identify the signing authority? When did we discuss the approval process? Who actually needs to say yes? If this stage feels messy, work backwards and tighten Stage 1.

• Create clarity around escalation.
  Don’t assume your AE knows when they can involve you or Finance. Be explicit. Sit down and define: At what discount level do you need approval? What terms are non-negotiable? When should we bring in Deal Desk? Reps negotiate more confidently when they know the guardrails. Create a Pricing and Discounting document that clearly outlines what they can offer independently, what requires manager approval, and what requires senior leadership approval.

🤝 Closing Thoughts

What I really like about looking at stage conversion this way is that it works on two levels.

At the individual level, you start to see skill patterns instead of just outcomes. When you can see those clearly, your coaching becomes more thoughtful. Instead of telling someone to “push harder” or “close faster,” you can say, “You’re strong at X, let’s focus on developing Y.” That’s a much more productive development conversation, and frankly, a much more motivating one.

When you zoom out and look at stage conversion across the team, you start to see whether what feels like a rep issue is actually a company issue.

• If Demo → Trial conversion is weak across the board, it might not be a discovery problem. It could be positioning, messaging, or ICP clarity. That’s a good conversation to have with Marketing and/or Lead Gen.

• If Trial → Contract is where things stall, you may need to look at the onboarding experience, product gaps, or how expectations are being set. That’s a great place to get feedback from and give feedback to Product.

• If Contract → Close is consistently messy, that’s often pricing structure, terms, or approval process. Chat with your Finance and leadership teams to get tighter alignment.

Stage conversion is so much more than just a sales metric. It can also be a really strong cross-functional diagnostic tool that helps you see whether you’re dealing with individual skill gaps or structural friction in your business. 🕵️‍♀️

Of course, it’s important that you know how to diagnose and coach to these trends as a leader. But the goal isn’t for you to be the only one spotting where things are breaking. The strongest teams are the ones where AEs can look at their own stage conversion and say, “I know where I’m strong, and I know where I need to tighten up.” That’s when the mindset shifts from “I show up and do my job” to “I own and drive my book of business.”

Next week, we’ll talk about how to help your reps zoom out, see their pipeline the way you see it, and take real ownership of how they generate, manage, and convert opportunities, not just execute the steps in front of them.

Till then! 🚙💨
Stacy

P.S. Before you go, I wanted to share a quick personal note. I’m currently supporting Blood Cancer United, and it’s something that means a lot to me. The funds raised go toward research that’s literally saving lives, as well as practical support for families navigating blood cancer, including helping parents take time off work to be with their kids during treatment. If you’re in a position to give, even a small amount truly makes a difference. You can donate here. I’m incredibly grateful for the support! 💛

📚 Stacy’s Book Challenge

This year’s goal is…81. 1 more than last year. 😮‍💨 Follow along as I try to get there.

As of this post, I have read 8 books. I finished The Strength of the Few earlier this week. Very proud that I knocked out another 700+ page book. 💪🏼 In my opinion, the second book wasn’t as good as the first…but I’m so bought in now, I feel like I have to read the 3rd when it comes out next year. Pray for me.

I’m currently reading:

• Odyssey - Still having a ton of fun, and it’s making me super hype for the upcoming Nolan movie adaptation!

• Anatomy of an Alibi - I just started today, so I’m not too far in. Taking a break from all these heavy books for some fun reading! 😻

Follow me on GoodReads! 🤓

• A forecast you can stand behind

• A clean CRM (which directly impacts how you model TOFU and future pipeline)

• Early indicators of trends, especially in Closed-Lost reasons

When done poorly, deals are discussed, but nothing gets clearer. There are no defined next steps. Timelines are based on what the buyer said once, weeks ago. Stages reflect hope instead of progress. Your AE says, “They love our product!” but can’t articulate the decision path, the economic buyer, or what has to happen between now and signature. 😣

That’s exactly why this meeting matters.

As a sales leader, this is your time to truly understand what’s happening in your business (I mentioned in my last post that I consider this a non-negotiable meeting to attend), while coaching your team to become elite sellers. 💰

Here’s how I like to structure a 30-minute pipeline review.

💻 A Quick Note on Setup

Before you get into coaching and deal strategy, let’s take a quick detour to talk mechanics.

As you can imagine, there are many ways to run a pipeline review. Most CRMs have a built-in forecast function, and I’ve found those to be pretty solid when configured correctly. You can also use Google Sheets or Excel, especially for earlier-stage companies.

Regardless of the tool, the key is that you have a system that is organized, consistent, and clean for both you and the rep.

You should be able to answer, at a glance:

• What’s getting called?

• What’s in play this month?

• What’s at risk?

• What’s likely slipping?

💡 Pro-Tip: I’m a big believer that AEs should be the ones leading their pipeline reviews, as they should know how to drive their book of business. If you’re the one asking, “What about Deal A? What about Deal B? What about Deal C?”, you might get the answers you need, but you’re not coaching them to think critically about their pipeline. The goal (other than revenue) is to build strong sellers who understand their numbers, their risks, and can orchestrate a sales plan without being prompted.

💍 Start With the Commit

Always start with what’s being called. Each rep should come prepared with:

• A commit number for the month

• The specific deals behind it (if they say, “I’m committing to $5,000,” but can’t tell you which deals are closing, you have a problem)

• Clear rationale for why those deals are closing

For a deal to be in commit, at minimum:

• Your company should be the vendor of choice

• There has been a verbal confirmation from the prospect of intent to move forward

• There is a defined (and reasonable) timeline

  • Even if the prospect says “yes,” does the AE have time before the end of the month to finalize redlines, complete the security review, go through procurement, and route for signature?

• The AE fully understands the buying process

It sounds pretty obvious, but you’d be surprised by how many AEs I’ve heard try to commit deals because the deal “felt good” (no, actually 😭). If a rep can’t clearly articulate why the deal will close this month, including the path to getting it done, don’t include it in your forecast (and push your AE for specifics, not sentiment).

🏃‍♂️ Active Deals (Prioritize This Month)

Next, move into active deals that could close this month. You do not need to review the entire pipeline if there are dozens of opportunities. Focus instead on:

• Deals closing within the next 30-45 days

• High ACV opportunities

• Deals that have slipped before

This is where a bulk of your coaching/guidance should happen. Here are a few ways we approach this section at SupplyPike:

• Get Specific on the Close Plan

  • Ask: “Walk me through the next 2-3 steps.”

  • Every in-month deal should have:

    • A scheduled next meeting

    • A clear deliverable (a 1-pager, a deck, the MSA, etc.)

    • Defined owners on both sides (What is the AE responsible for? What is the prospect responsible for?)

• Validate the Economic Buyer

  • Ask: “Do we know who signs? Have we spoken to them?”

  • If not:

    • What’s the path to get there?

    • Who is introducing us?

  • Late-stage deals that haven’t touched the decision-maker are riskier than they look - pay close attention to these.

• Pressure-Test the “Why Now”

  • Strong deals have urgency tied to:

    • Budget cycles

    • Operational deadlines

    • Executive mandates

    • Clear financial impact

  • If the “why now” is weak, there is a higher likelihood that the deal could slip.

  • This is usually a great coaching opportunity to make sure the AE has created enough value/urgency for the prospect. You could have the coolest tech in the world, but if there’s no real reason for the prospect to move forward, you won’t get a closed deal.

• Turn “Upsides” Into Commits

  • If a deal has a shot but isn’t ready for commit, ask: “What would have to be true to turn this from an upside into a call?”

  • Dig into:

    • What’s missing right now?

    • Who still needs to be involved?

    • What step hasn’t happened yet (legal, procurement, exec alignment)?

    • What has to happen this week to move it forward?

  • This gives the AE (and you) clear next steps to keep the deal moving forward.

• Protect Stage Integrity

  • If a deal has been sitting in the same stage for weeks, ask why.

  • If the criteria for advancement hasn’t been met, it shouldn’t move forward. That said, AEs should also be driving momentum with their opportunities.

    • Utilize historic data (where possible) to guide here. For example, if deals usually sit in the Contract Negotiation stage for two weeks and your AE has one there for four, that’s a flag. Either the deal isn’t real, or there’s something you can step in to help with.

This middle portion of the meeting is really about sharpening thinking. You’re not there to run the deal for them. You’re there to make sure every opportunity in the month has a real plan behind it. Over time (and I love this part 😍), this is where you’ll see reps start to level up. They start coming in more prepared. Their next steps get tighter, their timelines get more realistic, and you spend less time reacting to surprises and more time proactively guiding outcomes. It’s a beautiful thing.

🚪 Close Things Out (Literally)

The last 5-10 minutes of the meeting are about cleanup. This is where pipeline discipline really comes into play, and you close out deals that will not be moving forward.

When reps are closing deals, make sure:

• The correct Closed-Lost reason is selected

• Detailed notes are added (this will help when re-targeting down the road)

• The opportunity is truly dead

💡 Pro-Tip: I cannot overstate how important Closed-Lost discipline is for you as a Sales leader and for the rest of the org. Closed-Lost reasons are great leading indicators to better understand where you can and should expend your resources to better your sales motion. Here are a few common Closed-Lost reasons and what they might mean:

• Status Quo ➡️ Your AEs may not be building enough urgency or clearly quantifying the cost of inaction.

• Pricing ➡️ Your messaging may not be creating enough perceived value, or it might be time to reevaluate packaging or pricing strategy.

• Product Features ➡️ Valuable feedback to share with your product team. Is this a roadmap issue or a positioning issue?

• Chose Competitor ➡️ Time to look at competitive positioning. Are you losing on price, features, brand, or sales execution?

• Ghosted ➡️ This is often a signal that urgency was weak, value wasn’t clear, or the deal wasn’t multi-threaded (meaning the AE was relying on a single point of contact instead of engaging multiple decision-makers and influencers). Strong deals rarely disappear without warning.

Before a deal gets Closed-Lost (assuming it is qualified), ask:

• Did we multi-thread?

• Did we speak to the decision-maker?

• Did we quantify the pain?

• Did we explore alternative packaging or scope?

If the answer to any of that is “no”, challenge your AEs to explore the opportunity further. They should be very clear on why a deal is closing.

Quick note: There are different schools of thought on whether or not AEs should be allowed to Close-Lost deals independently. Personally, I prefer having this process flow through the manager. It creates healthy checks and balances, reinforces learning, protects data quality, and prevents deals from being closed before they’re truly done.

🔐 Pull Forward & Lock the Plan

In the last few minutes, look for anything that can be pulled into the current month. Sometimes there’s a deal sitting with a close date next month that can move forward with a little executive involvement, pricing flexibility, or a reference call. If acceleration is possible, assign the action in the meeting. Time kills all deals.

Round out your call with a recap of:

• The confirmed commit number

• Key risks called out

• CRM clean-up actions assigned

• Clear next steps for every in-month deal

Boom. You did it! 👏

🗑️ A Note on CRM Hygiene (and Why It Actually Matters)

Pipeline reviews aren’t just about calling deals. They’re also your built-in CRM checkpoint. This is where you make sure:

• Deal stages and projected close dates are accurate

• Dollar amounts are updated

• Dead deals aren’t lingering

• Notes are current

• Etc.

Poor CRM hygiene doesn’t just create messy dashboards. It directly impacts your forecast, skews your conversion data, and eventually impacts things like hiring and capacity planning. If close dates or dollar amounts are inflated, your pipeline looks healthier than it actually is. If stages don’t really mean anything, your conversion rates become unreliable. And if dead deals sit open “just in case,” your coverage math starts lying to you.

No bueno. 🙅🏻‍♀️

Pipeline reviews are also a great place to step back and ask: Do we actually have enough real opportunity in the pipe?

In Part 2 of Pipeline Planning, we talked about Conversion Rates. If a rep needs to close $3,000 MRR per month and your historical close rate is 33%, they need roughly $9,000 MRR in qualified opportunity to realistically hit that number. If, when going through their pipeline review, you find they only have $5,000 in legitimate opportunity, this could be a signal that something upstream needs attention.

Good pipeline reviews protect the current month. Great ones protect the next two.

📈 Final Thoughts

A good pipeline review isn’t about creating pressure or catching people doing something wrong. It’s about making sure you actually understand what’s happening in your business instead of finding out at the end of the month when it’s too late to adjust.

When you run this meeting well, a few important things start to compound. Your forecast becomes more stable because it’s grounded in reality. Your reps start thinking more strategically about their deals because they know they’ll have to articulate the “why” behind their calls. Your CRM gets cleaner because it’s being actively managed, not passively updated. And over time, you build sellers who truly understand their book of business.

Pipeline reviews aren’t just a forecasting exercise. They’re one of the most consistent coaching moments you get as a Sales leader. Treat them with the respect they deserve!

Next week, I’ll share how we use stage-to-stage conversion data to spot strengths and gaps across reps. Sometimes an AE is excellent at generating interest but struggles to close, or another is a weak opener, but is great at converting once they get their prospect to a trial. Pipeline data makes that visible so you can train intentionally across the team.

Happy selling! 🤙
Stacy

📚 Stacy’s Book Challenge

This year’s goal is…81. 1 more than last year. 😮‍💨 Follow along as I try to get there.

As of this post, I have read 7 books. I knocked out The Curious Incident of the Dog in the Night-Time pretty quickly, as well as Dr. Jekyll and Mr. Hyde (that one was wild).

I’m currently reading:

• The Strength of the Few - I’m about 70% through, going way faster than the first book 🙏

• Odyssey - I’ve read all the other books in Stephen Fry’s Great Mythology series - SO GOOD. Also gearing up for the upcoming Nolan movie adaptation 👀

Follow me on GoodReads! 🤓

Strong meetings can create clarity, alignment, and momentum. Poorly designed ones can quietly drain time, energy, and trust, and earn you the dreaded “this could have been an email.” 😭

At SupplyPike, we use lightweight, repeatable meetings inspired by agile development (and adapted from other great teams, as Christine wrote about earlier this week) to create fast feedback loops and alignment across Sales, internally, and across the broader org. If you’ve never had to run meetings before, or are starting to figure out a cadence that works for your team, use this as a cheat sheet to get started.

👋 Sales / BDR All-Hands

When: Weekly, Mondays

Duration: 30 minutes

Who It’s For: AE and/or BDR team members

When you’re a smaller team, it can make sense to have everyone in one meeting. As you grow and scale, you can split this into separate AE and BDR meetings. The trigger is simple: when it stops being impactful for either team and starts taking away valuable calling or selling time.

Purpose:
Create shared context across the AE and/or BDR teams so everyone has visibility into goal attainment, what’s changing, and weekly priorities

Why It Matters:

• Ensures AEs and/or BDRs hear the same updates at the same time

• Reduces “I heard this from so-and-so” confusion

• Helps newer team members understand how Sales, BDR, Product, and Marketing connect

• Keeps big updates out of 1:1s or from getting lost on Slack

Typically Covers:

• High-level goal and performance updates (monthly/quarterly/annual attainment)

• Process or policy changes (e.g., CRM process updates, announcements about new SPIFFs, etc.)

• Product or feature announcements (a great opportunity to bring in Product leaders)

• Marketing initiatives and campaigns

• Market or competitive changes

• Anything broadly relevant to how the Sales team operates

🎩 Sales Leadership Sync

When: Weekly, Mondays

Duration: 60 minutes

Who It’s For: Sales leaders

Purpose:
Ensure leadership alignment before direction cascades to teams

Why It Matters:

• Prevents conflicting guidance

• Identifies cross-team issues early

• Enables faster, better decisions

• Keeps the operating system coherent

Typically Covers:

• Alignment on current revenue performance and forecast confidence

• Team capacity, coverage, and resourcing risks

• Cross-team issues or dependencies that need resolution

• Upcoming changes that will impact the sales org (process, comp, staffing, messaging)

• Decisions or guidance that need to be aligned on

💡 Leader Note:

This is your time as a Sales leader to hear what’s really happening on the ground. Your managers are closest to the work and the people doing it. They have a real sense of how the team is feeling.

I usually spend the first 15–30 minutes on “real work” with my team (checklists, decisions, and blockers). The rest of the time is where the real value is: candid conversations aka the “real real”. This meeting is also a great place to slow-roll ideas. If there’s something you want to try, you can gut-check it with your managers before rolling out something that may feel totally tone-deaf.

Finally, this is where you set the tone. When leaders leave this meeting clear, energized, and aligned, they carry that clarity back to their teams. Inspire your managers here, and they’ll inspire their teams everywhere else.

🚰 Pipeline Reviews

When:

• SMB: Weekly

• Enterprise: Biweekly

Duration: 30 minutes per person

Who It’s For: AEs and their Sales Manager

Purpose:
Review active deals, pipeline health, and near-term priorities, with depth calibrated to deal size and sales cycle

Why It Matters:

• Keeps pipeline data accurate and trustworthy

• Enables coaching on real, active deals

• Surfaces risk early and reduces end-of-month or end-of-quarter surprises

• Reinforces disciplined deal strategy, prioritization, and planning

Typically Covers:

• Review of deals called or committed for the month/quarter

• Discussion of deals that should be Closed-Lost and removed to keep the pipeline clean

• Identification of high-priority or stuck deals where manager or leadership support could unblock progress

💡Leader Note:

As a Sales leader, I believe that pipeline reviews are meetings you should attend as often as possible. Even today, I sit in on close to 20 a week when my schedule allows. They give you a real, unfiltered finger on the pulse of your GTM motion, and most importantly, what attainment is actually likely to look like.

If you’re unable to attend these due to time or your team’s size, I recommend setting up a weekly Pipeline Rollup with your Sales managers to discuss what’s being called/committed for the month.

💖 1:1s

When: Weekly or biweekly

Typically, I recommend hosting weekly 1:1s for newer or more junior sales team members to ensure they get the guidance they need. Once they (or you) feel comfortable, you can move these to biweekly, unless they prefer weekly.

Duration: 30 minutes per person

Who It’s For:
AEs/BDRs ↔ Manager
Managers ↔ Sales Leader

Purpose:
Dedicated time to discuss workload, priorities, and growth (Pro-tip: This is NOT Pipeline Review 2.0)

Why It Matters:

• Keeps workload sustainable and priorities clear

• Creates space for coaching and skill development - your job as a leader is to help people grow, not just perform

• Separates “the number” from the human

• Builds trust and psychological safety

• Creates space for honest, two-way feedback

Typically Covers:

AE/BDR ↔ Manager

• Individual performance and development

• Skill building, confidence, and career growth

• Day-to-day blockers and support needs

Manager ↔ Sales Leader

• Team health and performance trends

• Staffing, coverage, and capacity risks

• Manager development and consistent leadership across teams

💡Leader Note:

I’m big on letting individuals dictate what they want to talk about in their 1:1s. This is their time. I usually cover anything important that I need to share (if necessary), then let them drive the conversation.

Wherever possible, do not move these meetings. Treat them as sacred. When everything else takes priority, you’re sending a very clear signal about what you actually value.

1:1s are where real issues surface early, before they turn into missed numbers, burnout, or disengagement. They create space for honest conversations about what’s going well, what’s hard, and what support is actually needed. In my experience, leaders who protect this time get better performance because they get better signals, stronger alignment, and teams that feel invested in what they’re building. Treat these meetings with the respect they deserve!

🥊 Closed-Lost Reviews (SMB & Enterprise)

When: Quarterly

Duration: 30-60 minutes

Who It’s For: Sales, Product, Marketing

In the early days, if there isn’t a clear distinction between SMB and Enterprise pods (or whichever pods your business has), it’s perfectly fine to run these reviews together. As your sales motions become more defined, you can separate them, but do so intentionally. These meetings pull in not just Sales, but also Product and Marketing, so time and focus matter.

I also recommend including AEs when the team is small. As you scale, you can transition to having Sales managers represent their teams and speak to broader trends they’re seeing across deals.

Purpose:
Turn lost deals into learnings and share trends with other cross-functional teams

Why It Matters:

• Identifies patterns across lost deals

• Surfaces gaps in product, messaging, or qualification

• Helps Product and Marketing prioritize improvements

• Improves future win rates through shared insight

Typically Covers:

• Patterns and trends across Closed-Lost deals (not just individual outcomes)

• Discussions around common loss reasons (pricing, timing, product gaps, competition, internal alignment, etc.) - why is it happening and what can be done about it?

• Where deals are breaking down in the sales process or buyer journey

• Signals that could have been caught earlier in qualification or discovery

• Clear takeaways that can inform future messaging, product priorities, or sales motion adjustments

💡Pro-Tip: It’s fine to reference individual deals for color and context, but try not to get stuck there. One deal’s outcome doesn’t automatically translate into a change for every future deal. The real value of Closed-Lost reviews comes from identifying recurring patterns and acting on them. Quarterly reviews give you enough volume to see trends clearly.

📣 Leadership Cross-Functional Revenue Review

When: Weekly or Biweekly

Duration: 60 minutes

Who It’s For: Leadership (Sales, Finance, Customer Success, Product, Tech Marketing, Ops)

Purpose:
Review revenue performance and broader trends across the org

Why It Matters:

• Connects frontline execution to company-level outcomes

• Creates a shared understanding of revenue drivers and risks

• Aligns leadership on forecasts, headcount, and strategy

• Prevents Sales from operating in a silo

Typically Covers:

• Revenue performance against monthly, quarterly, and annual goals

• Funnel health and leading indicators (e.g., demos, conversion rates, pipeline coverage, etc.)

• BDR insights on what’s working, what’s not, and where lead quality or volume is shifting

• Marketing updates on upcoming campaigns, launches, or messaging changes

• Product and technical updates on near-term feature releases or roadmap items that impact selling

💡 Leader Note:

This meeting works best when it includes the functional leaders closest to execution (Sales, BDR, and CS managers, and heads of Product, Tech, Marketing, Finance, and Ops). The goal is for everyone to understand the sales metrics first, then use that shared context to call out trends, friction, and opportunities from their perspective.

This is not an executive leadership meeting focused on high-level company strategy. It’s an operating forum. The purpose is to keep cross-functional leaders informed on what’s actually happening in Sales and create space for real discussion: what’s driving results, where things are breaking down, and how other teams can help close gaps.

In practice, this is where a lot of the best ideas surface. You get input you wouldn’t otherwise hear, avoid solving sales problems in a vacuum, and benefit from the layer of leadership that’s closest to the work.

💁🏻‍♀️ Final Thoughts

You don’t need all of these meetings on day one. Use what makes sense for where your company is right now, not where you hope to be six months from now. Your calendar will thank you for it.

At a minimum, start with a strong all-hands, consistent 1:1s, and regular pipeline reviews. Those three alone will give you clarity, accountability, and early signals. From there, add meetings intentionally as your team grows, deal complexity increases, and cross-functional coordination becomes more important.

If you’re building this from scratch:

• Start with clarity, not volume

• Be explicit about each meeting’s purpose

• Kill meetings that don’t earn their keep

  • Every meeting has a job. When it stops doing that job, it should change or go away. At SupplyPike, we even do an annual meeting audit to review what still makes sense to keep and what to remove. Don’t fall in love with meetings for meeting’s sake! 🙅🏻‍♀️

Meetings aren’t the work, but they shape how the work gets done. The best leaders don’t run more meetings; they run better ones. When meetings are designed with intention, you and your team will feel the difference.

Next week, we’re digging into pipeline reviews: how to make them more useful, keep your CRM honest, really understand your forecast, and coach AEs in a way that keeps them growing.

Go sell something! 💰
Stacy

📚 Stacy’s Book Challenge

This year’s goal is…81. 1 more than last year. 😮‍💨 Follow along as I try to get there.

As of this post, I have read 5 books. Woohoo! I finally finished The Will of the Many and East of Eden. TWOTM was excellent for world-building - highly recommend if you enjoy YA fantasy. Also easy to see why East of Eden is an instant classic…”And now that you don’t have to be perfect, you can be good.” What an absolute banger of a quote. Also, there’s going to be a Netflix adaptation coming next year, so that’s exciting!

I’m currently reading:

• The Strength of the Few - yes, I gave myself another 700-page book to read 😭

• The Curious Incident of the Dog in the Night-Time - read this years ago and excited for a re-read!

Follow me on GoodReads! 🤓

By now, you’ve probably done more math than you care to admit, had a lot of (mostly productive 🙂‍↕️) planning conversations with leaders across your org, and hopefully aligned on where revenue is coming from, who is responsible for generating it, and when, where, and how that capacity comes online. The Sales team is ready to go, so let’s tackle the last piece of this puzzle…how do you actually pay them?

Comp plans are about more than just motivation. They’re one of the clearest signals you can send to your team about what matters to the business. People will always follow the money, so your incentives must reinforce the behaviors you want to see.

Let’s get into it.

💰 Paying AEs

Most B2B SaaS Account Executives are paid on an On-Target Earnings (OTE) model.

🍌 Base / Variable Split

OTE represents what a rep earns when they achieve 100% of quota and is typically made up of two components:

• Base salary is what a rep earns regardless of performance

• Variable compensation or On-Target Commission (OTC) is what a rep earns by closing deals and is directly tied to quota attainment

  • Reps earn 100% of OTC when they hit 100% of quota

A 50/50 split between base and variable is pretty typical across the industry. It is familiar to candidates, easy to explain internally, and flexible enough to work across a wide range of sales motions. That said, the right split depends on where you are in your company’s journey.

Earlier-stage companies or newer sales motions often lean toward a higher base (for example, 60/40) to protect sellers while the model is still stabilizing. More mature, highly repeatable motions with experienced sellers may skew more heavily toward variable compensation. I’ve seen splits as aggressive as 30/70! 😱

Neither approach is inherently better. The right answer depends on how confident you are in your pipeline generation, quota-setting, and overall sales motion. Paying people as if everything is solved when it isn’t is one of the fastest ways to lose strong talent. For example, if you don’t have product-market fit yet but expect reps to earn most of their pay through commission, you’re asking for trouble. If you’re still learning what “good” looks like, starting with a 50/50 split is a perfectly reasonable place to begin.

Before we dive into a step-by-step of putting together an AE’s comp, I wanted to introduce a few helpful concepts.

📊 Quota:OTE Ratio

The quota:OTE ratio is a quick gut check to make sure a sales role works for both the business and the rep. It helps answer a simple question: Are expectations ambitious without being unrealistic?

The ratio compares how much revenue a fully ramped rep is expected to generate (quota) with what they earn for hitting that number (OTE). Many startups land in the 5x–10x range because it balances efficiency for the company with goals that reps can reasonably achieve.

Where you land in that range depends on your business. If you sell a clear “need,” have a higher ACV, or operate in a less competitive market, it’s often reasonable to expect more revenue per rep. If you sell a lower-cost product in a crowded space, deals are harder to win, and expecting the same output may not be realistic.

This metric isn’t about squeezing more out of people. It’s a guardrail to help you set expectations that reflect the reality of your market and GTM motion.

💸 Commission %

You’ll often see 10% cited as a common SaaS benchmark, and for many companies, that can be a helpful reference point. Historically, that number came from models where AEs were responsible for generating much of their own pipeline.

That isn’t true for every startup, and these days, it’s becoming increasingly less common. Many teams today invest in BDR roles so AEs can focus on discovery, deal strategy, and closing. When pipeline generation is shared across roles, it’s normal for commission rates to differ from older benchmarks.

What matters most isn’t the exact percentage, but whether the plan makes sense in context. Deal size, win rates, lead quality, sales cycle length, and how much of the funnel the AE owns all matter. In some businesses, a slightly lower commission rate can still result in strong earnings because deals are larger, more predictable, or easier to win.

If you’re new to startups, it’s important to know that there isn’t one “correct” number. Commission rates vary widely, and what’s fair depends on how your entire sales motion is designed. The goal is to build a system where reps feel fairly rewarded and the business can scale responsibly.

Okay - let’s jump into a quick example! 🧮

Step 1: Start with quota

We’ll use the SMB AE Quota example of $600,000 from Part 3.

Step 2: Use market data

Establish a reasonable base salary for the role you’re evaluating, making sure it reflects the right geography and experience level. Glassdoor is a common salary comparison site, but you can use whichever one makes the most sense for your industry.

Let’s say the midrange point for an SMB AE in our region is $50K.

Step 3: Layer on Base/Variable Split

Say the 50/50 split makes sense for your team. That would bring an SMB AE’s OTE to $100,000 ($50,000 Base / $50,000 Variable).

Step 4: Check Quota:OTE Ratio

This is a good place to do a temperature check to make sure your quota and OTE are playing well with each other.

Quota:OTE Ratio = Quota ÷ OTE

In this example, $600,000 divided by $100,000 yields a 6x ratio, which sits comfortably within the typical range.

💡 Pro-Tip: If your ratio is too high, it’s usually a signal that quota expectations may be unrealistic for the current motion. You may need to lower quota and/or increase headcount, or revisit assumptions around pipeline or conversion. If it’s too low, it can indicate inefficiency on the business side, meaning revenue per rep may not justify the cost of the role, and the model may struggle to scale.

Step 5: Check Commission %

Finally, calculate the effective commission rate by dividing the variable component by quota.

Commission % = OTC ÷ Quota

Here, $50,000 divided by $600,000 results in an 8.3% commission rate, which may be appropriate depending on how your broader GTM model is structured.

All told, this is a fair comp recommendation for an AE, based on the assumptions we utilized. ✅ Again, we’re using a lot of round numbers and examples here - work with your finance team to make tweaks to your roles as necessary!

🤠 Paying AMs

From a comp standpoint, Account Managers often look very similar to AEs. They’re typically paid on an OTE model with a base and variable component and carry a quota tied to a defined book of business. In practice, you can usually follow the same steps as AE comp: start with quota, layer in market data, and pressure-test the math.

Where AM comp requires a bit more thought is in what you’re actually asking the role to do. 🤔

In many organizations, AMs are responsible for a combination of expansion or upsell revenue, renewals, and broader retention metrics such as Gross Dollar Retention (GDR) or Net Dollar Retention (NDR) (peep Part 1 for a refresher on these metrics 👀). Because the role can span so many outcomes, how you weight incentives should be very intentional. What you pay for is what gets prioritized.

A 60/40 split is fairly standard for AM roles, especially when there is a clear expectation that AMs will grow accounts through expansion or upsells. Because they work within existing relationships rather than closing entirely new deals, the role typically carries less variable risk than an AE position. This is not a one-size-fits-all rule, though. If your product has limited expansion opportunities and the role is primarily focused on retention and renewals, it may make more sense to skew further toward base (for example, an 80/20 split) and tie variable compensation more directly to keeping customers successful and retained.

💡Pro-Tip: Retention metrics like GDR or NDR don’t need to be tied to traditional commission percentages. Especially for newer teams, these are often easier to structure as periodic bonuses, such as a quarterly payout for hitting renewal or retention targets. This approach keeps the plan simpler and makes it clearer how performance is being evaluated.

The key for this team is focus. 🧘🏻‍♀️ Because AMs are asked to do a lot, equally weighting everything can unintentionally signal that nothing is truly important. Start by identifying the behaviors and outcomes you most need from the role today, design incentives around those priorities, and layer in additional complexity later.

📧 Paying BDRs

As with AEs and AMs, most BDR roles use an OTE-style model, but typically with a higher base and smaller variable component. A 75/25 split is common in the industry, as the role sits earlier in the funnel and is often filled by less experienced sellers. A higher base reduces risk for your reps while still rewarding performance.

Variable compensation is usually anchored to a single, clear output, most often qualified demos or meetings held. Whatever metric you choose (I wrote a long TED talk about why I’m a fan of demos completed in Part 2 😅), it should map cleanly to how you modeled your funnel so expectations stay aligned across roles.

A simple way to sanity-check BDR comp is to look at the cost per demo. Divide total variable compensation by expected demos, then compare that cost to the value of the deals those demos produce. Paying $100 for demos that lead to $5,000+ in ARR may be reasonable. Paying $100 for demos that convert to $500 contracts likely is not. That demo cost ultimately rolls into CAC, which is a broader efficiency conversation for another day. 😌

As with other roles, resist the urge to overcomplicate this early. Anchor incentives to one primary outcome, use SPIFFs for short-term priorities, and adjust as your funnel and economics become clearer.

🍻 Putting It All Together

Now that we’ve covered individual roles, let’s talk about what applies to everyone: timing, cadence, and payout mechanics.

🛹 Ramping: Setting New Hires Up for Success

What we discussed above refers to instances where reps are fully ramped. That won’t always be the case. There are tons of approaches to ramp compensation, and each can make sense depending on the complexity of your sale and the maturity of your onboarding process. I’ll share a few examples below…

• No ramp guarantee
  Reps earn commission only when they close deals. This can work well when ramp is short, onboarding is highly structured, and new hires can reasonably expect to close quickly.

• Ramped guarantee
  A portion of variable compensation is guaranteed early on and gradually phases out. For example, reps might receive 33% of their variable comp in month one, 66% in month two, and move fully to performance-based pay by month three. This works well when ramp requires learning a more complex product or sales motion.

• Temporary guarantee
  Reps receive a fixed percentage of their variable compensation (for example, 75-80%) for a set period before moving fully onto plan. This can be helpful when early performance is influenced by factors outside the rep’s control, such as long sales cycles or limited pipeline at hire.

• Recoverable draw
  In this model, reps are paid variable compensation upfront and are expected to “earn it back” through future commissions. If they don’t, the balance carries forward. My hot take - not a fan. 🙅🏻‍♀️ While this approach still exists, it often creates unnecessary pressure and can feel like asking reps to take on financial risk simply for joining the company. In practice, it tends to undermine trust more than it drives performance.

Whatever you choose, what matters most is clarity and fairness.

📆 Compensation Timing and Goal Cadence

There are many ways to structure goal timing and payout cadence, including monthly, quarterly, and annual approaches. Each has tradeoffs.

Whenever possible, I strongly prefer annual goals. Earlier in SupplyPike’s growth, we adjusted goals quarterly, and it created unnecessary friction. Attainment became harder to track, motivation suffered, and the constant movement of goalposts made it difficult for reps to plan their efforts.

What has worked well for us instead is setting a clear annual goal, with monthly pacing for visibility, and introducing accelerators once the annual goal is achieved. For example, if a rep hits their number in September, every incremental dollar after that is paid at a higher rate. This approach reduces sandbagging behavior, eliminates the “starting over” mentality, and incentivizes reps to hit their annual number as quickly as possible. It benefits both the rep and the business.

🤑 Accelerators and Overperformance

Accelerators are designed to reward overperformance and encourage reps not just to hit 100% of their goal, but to crush it. 👏🏼 There are many ways to design them, but the intent should be consistent: make overachievement meaningfully rewarding. An example could be:

• 0-100%: 1x Commission Rate

• 100-120%: 1.5x Commission Rate

• 120%+: 2x Commission Rate

This is why goal-setting is so important. If goals feel unattainable, reps disengage. If they are too easy, the business overpays for marginal performance. Uncapped commission can be a powerful tool here, allowing top performers to win big while often still being more cost-effective than adding headcount to achieve the same results.

🌋 SPIFFs as a Tactical Tool

SPIFFs (short-term performance incentives) are temporary rewards used to drive very specific behaviors for a limited period of time. They’re also where you get to have a little fun. 🤩 For teams like BDRs, SPIFFs are a great way to influence short-term priorities without hard-coding everything into the comp plan. At SupplyPike, we set aside a small quarterly SPIFF budget and give managers flexibility to run incentives aligned to whatever the business needs in the moment.

The key is that SPIFFs are meant to be temporary. They’re a way to experiment, nudge behavior, and create energy and excitement within your team without constantly rewriting your compensation plan. Whether you formalize them or keep them lightweight depends on your culture, but used thoughtfully, they’re a great complement to your core incentives, and a nice reminder that not everything has to be permanent to be effective.

🦾 Payout Mechanics and Transparency

In B2B SaaS, monthly commission payouts are pretty standard, usually paid after month close so deals can be validated. Obviously, your finance team should have some pretty heavy say in how this works. While a consistent cadence matters a lot to Sales teams, so does the issue of transparency.

It goes without saying, but reps should never feel like commission is a black box. Every rep should understand what they’re getting, when, and why. In the early days of SupplyPike, I remember a BDR saying, “I don’t know what I’m getting paid, I just wait for the commission check to hit.” 💀 That was big pivot point for us in making sure we got that fixed as soon as possible.

Early on, this might look a little scrappy…spreadsheets, manual reports, a quick approval flow. And that’s okay. What matters is that reps can see their numbers, understand how they were calculated, and spot issues before payroll hits. As you scale, tooling will make this easier, but the principle stays the same.

When reps trust the math, they stay focused on selling. When they don’t, you end up re-explaining the comp plan every single month.

✍🏼 Terms, Conditions, and Goal Sheets

This part is not optional, and future you will be very grateful you did it.

Every rep should sign two things: a Terms & Conditions document and an individualized goal sheet. At a minimum, your Ts & Cs should cover:

• Payment timing and payout cadence

• Definitions of what counts as a closed deal

• Commission calculations and data sources

• Deal splits, crediting rules, and edge cases

• Treatment of churn, clawbacks, or revenue reversals

• Quota, territory, or role changes mid-plan

• Leaves of absence and ramp interruptions

• Performance expectations and underperformance

• Dispute resolution and final decision authority

• At-will employment and plan change language

I highly recommend taking the time to walk through these documents with your team before they sign. Explain what they’re agreeing to and why. When questions or disputes come up later (and they will), you’ll have a shared reference point, which makes conversations that much easier to manage.

🥂 Closing Thoughts

Kudos again for making it this far! 👏🏼

Building compensation plans is not the most glamorous part of scaling a company, but it’s one of the most important, and you’ve now worked through the hardest pieces. When they’re designed thoughtfully, they reinforce your strategy, motivate the right behaviors, and scale with your business. When they’re not, they quietly create friction, confusion, and very expensive surprises.

Design them with intention. Your team will feel the difference!

I’ll be back next week to chat about meeting cadences - what should you be meeting about and when, and how do you prevent your team from thinking “this should have been an email?”

‘Til then! 👋🏼
Stacy

📚 Stacy’s Book Challenge

This year’s goal is…81. 1 more than last year. 😮‍💨 Follow along as I try to get there.

As of this post, I have (still only) read 3 books. I have no excuses. 😔

I’m currently reading:

• East of Eden - about 90% through now!

• The Will of the Many - about 70% through now!

Follow me on GoodReads! 🤓

At this point, you’ve put in a lot of work. You’ve taken an ARR target, segmented it into clear revenue goals by pod and team, and translated those goals into pipeline requirements and channel volume.

So…you should be able to just sell stuff, right? …right?

Part 3 of our series tackles the question:

Do we have the right people, in the right roles, at the right time, to make this plan real?

This is where bottoms-up planning comes in. Strategy only becomes executable when it’s grounded in headcount, capacity, and what your team can realistically deliver.

Let’s get into it.

📝 Getting Started: AE Planning

Let’s start where most revenue plans start: new sales AEs.

AE planning is usually the cleanest place to begin because it ties most directly to revenue targets. Once you can sanity-check capacity here, the same logic can be applied (with a few twists) to expansion, top-of-funnel, and other supporting roles.

Before you get fancy, start with a very simple question:

I need $X in revenue from this pod. Historically, one IC in this pod produces $Y. Do I even have enough people to make this possible?

Continuing the example from Part 1:

• Revenue needed from the SMB pod: $1,440,000

• Example historical production per fully ramped SMB AE: $600,000

At a high level, this tells us we need ~3 fully productive reps to support the goal. If we only have 1 rep in seat today, we already know the plan breaks without additional headcount, regardless of how good our pipeline math looks.

This quick check prevents you from building detailed forecasts on top of an impossible foundation.

🤧 From Napkin Math to Real Planning

Once you’ve established a rough headcount requirement, you can move into a more disciplined bottoms-up process to refine timing, assumptions, and tradeoffs.

Step 1: Validate Current AE Headcount

Start with the team you actually have:

• Fully ramped AEs

• Partial productivity for newer/ramping reps

• Known scope or territory changes

This establishes your true baseline capacity.

Step 2: Layer in Planned Hires and Ramp Timelines

Next, fill the gap between where you are and what the napkin math says you need. This includes:

• Planned hire dates

• Role-specific ramp timelines

• Partial productivity during ramp months

This step often surfaces uncomfortable truths. If the model says you need 3 reps by June but hiring can’t realistically start until August, something has to give: the goal, the timing, or the plan. These are conversations you should be having early and often.

🚨 Step 2.5: Sanity Check Against Budget 🚨

Before you finalize hiring assumptions, you need active alignment with your CFO, VP of Finance, HR, or whoever owns the budget.

That means pressure-testing:

• Whether the headcount you’re modeling is actually approved or fundable

• How hiring timing affects cash flow and burn

• Whether assumptions fit within the budgeted OPEX

You can build the most elegant capacity model in the world, but if Finance isn’t aware of (or aligned with) the plan, you’re setting yourself up for a painful surprise later. 🥵

At SupplyPike, we typically kicked off budgeting discussions for the following year with our Finance team as early as Q3, which gave us time to make adjustments in Q4 and enough flexibility to adapt as the second half of the year evolved.

Step 3: Model Productivity Using Real Performance

With headcount, timing, and budget alignment in place, you can model expected productivity using historical performance, checked against industry benchmarks.

In a healthy, well-calibrated sales org, performance roughly follows a bell curve:

• ~80% of reps land around ~85% attainment
  ➡️ These are solid performers doing the job you hired them to do

• ~10% of reps meaningfully exceed quota
  ➡️ These are your top performers who should be hitting accelerators and earning outsized rewards

• ~10% of reps will likely, unfortunately, fall short
  ➡️ These reps typically need coaching, role changes, or, over time, to be managed out

If most of your team consistently sits below ~85% attainment, your goals, timing, or capacity assumptions are likely too aggressive. If most reps are cruising past quota and hitting accelerators, your quotas are likely too low, and comp may be misaligned.

📆 Annual and Monthly Variability

Even with well-calibrated assumptions, performance doesn’t typically distribute evenly across the year. Most B2B SaaS businesses experience:

• Stronger quarters tied to budget cycles or renewal windows

• Softer periods around holidays, summer months, or fiscal year resets

• Event-driven spikes that pull demand forward

Ignoring this can lead to trouble. Your annual plan may be right, but monthly pacing will feel off. It’s important to ensure your hiring/ramping plan accounts for the variability of your business’s performance.

✍🏼 In Practice: Putting It All Together [AEs]

You can model this however makes the most sense for your company.

If you have a dedicated planning tool, great, use it! If you don’t, Excel or Google Sheets work just fine (don’t @ me about the Microsoft Suite, ok 😭). For early-stage teams (and many later-stage ones too), a well-structured spreadsheet is often clearer, more flexible, and easier to share with your team.

Here’s a simple example of what this can look like…

A few callouts:

• Hiring timing is explicit. In this model, we’ve shown hires landing in January and March. Calling out hire months forces you to think about when capacity actually opens up, not just that it exists somewhere in the plan.

• Ramp assumptions are intentional. In this example, we’ve assumed a ramp-up period of one month at ~50% productivity, but this is highly dependent on your specific business.

  • If you have a simple product or short sales cycle, reps may contribute meaningfully almost immediately.

  • If your product, sales motion, or deal cycles are more complex, bake that into your planning. Underestimating ramp can set you and your new reps up for failure.

• This model shows the difference between theoretical and realistic outcomes. If every rep hits 100% of quota, the team clears the annual goal. But we all know better by now. 😌 When we apply a more realistic 85% average attainment (or whatever threshold you’ve chosen), the plan comes up short.

  • 💡Pro-Tip: Once you’ve built the full model, it’s worth reviewing it month by month, not just annually. If a given month carries a $72K target but you don’t have enough active, ramped capacity to hit that number, that month is effectively a planned miss. Peep January in the image above, for example. 👀

  • Seeing the monthly or annual shortfall at this stage of planning gives you options:

    • Adjust the annual goal (not ideal, but sometimes necessary)

    • Redistribute monthly goals (where it makes sense)

    • Add headcount, if budget allows

    • Pull hiring forward to capture more productive months

    • Revisit quota or productivity assumptions

This turns your model into an actual decision-making tool that you can use to collaborate across the entire org.

💡 Quick note if you don’t have historical performance:

That’s okay, especially early on. Anchor instead on industry benchmarks:

• Research benchmarks specific to your segment, ACV, and sales motion

• Use a ~5x–10x Quota:OTE ratio as a baseline for revenue-generating roles (we’ll dig into this more in Part 4! 👀)

From there, you can back into reasonable quotas and productivity assumptions. As you collect real performance data, replace assumptions with reality and tighten the model over time.

📈 Layering in AM Planning

For Account Managers, we follow the same planning process outlined above, with one added constraint: the book of business. You still:

• Start with napkin math

• Validate current headcount

• Layer in hires and ramp

• Model to realistic attainment

But before locking anything in, add one more required step…

Step 4: Balance Productivity Expectations Against the Book

Validate that the AMs’ books actually contain enough opportunity to support the expected level of expansion. For example, if you expect $100K in expansion from an AM but their book is small, fully sold-in, or high-risk, they’ll never get there, no matter how good they are.

📊 Adding AMs to the Model

There’s no single “right” way to model expansion. Personally, I’ve always treated AM planning as part of core revenue planning. Practically, that means AMs live in the same model as new sales, right alongside AEs, rather than in a separate spreadsheet or tab.

In the example above, you’d add AMs to the same modeling tool, including:

• Their expected expansion contribution

• Any ramp or transition periods

• And the same 85% attainment assumption

This makes it immediately obvious how new sales and expansion work together to hit the total number, and where gaps emerge if one side underperforms.

🤳🏼 BDR Planning

BDR capacity planning follows the same core process as AEs and AMs, with a shift in focus. Rather than planning for revenue, BDR planning is about timing and throughput. Specifically, ensuring the right volume of qualified demos enters the system early enough to support future revenue.

A few things to keep in mind:

1. Cycle Time Matters

Say your average sales cycle is two months. That means that demos need to be booked two months before the revenue you expect to close. If you’re planning for the new year, January revenue depends on demos happening in November. ‼️ BDR capacity should be planned ahead of revenue targets, especially when phasing monthly goals or setting hiring timelines. You may have different sales cycles depending on the pods you’re supporting - plan accordingly.

2. Seasonality Still Applies

Seasonality affects BDRs differently than it affects Sales. Sales performance often tracks to budget cycles and fiscal calendars, while BDR performance is more closely tied to buyer availability, aka when people are actually in the office and willing to take meetings. Planning BDR capacity around human availability, not just revenue calendars, helps avoid misdiagnosing timing issues as performance problems.

3. Events Create Spikes (Plan for Them)

Events (like attending trade shows or marketing pushes) introduce predictable spikes in demo volume that should be planned for explicitly. Portion incremental demo targets to event-heavy months rather than smoothing goals evenly across the year. Otherwise, reps appear to overperform during events and underperform in quieter months, even when execution is consistent.

BDR is the timing layer of the revenue engine. When it’s aligned, the rest of the plan holds. When it’s not, teams often try to compensate downstream with AE or AM effort, which is no fun for anyone! 😾

✍🏼 In Practice: Putting It All Together [BDR]

You can model BDR headcount and capacity planning pretty similarly to the AE spreadsheet above.

Here’s another simple example of what this can look like…

A few callouts:

• Ramp assumptions are intentionally shortened. In this example, BDR reps reach full productivity by their second month to illustrate what a shorter ramp can look like. As before, flex ramp timing up or down based on your onboarding complexity, tooling, and expectations. As a general rule, AEs should take longer to ramp than BDR reps.

• Event spikes and holiday dips are modeled. For our demo company, demo targets flex upward during the summer months to account for a hypothetical heavier event schedule, then taper in Q4 due to holidays and reduced buyer availability. As always, plan for what actually makes sense for your business.

  • 💡 Pro-Tip: In this example, lower demo volume in Q4 = lower revenue in Q1 of the following year. Make sure you’re taking BDR timing and sales cycle length into account when planning revenue - one directly impacts the other.

• The model also surfaces optimization opportunities. Here, the team ends the year roughly 40 demos over target, even after applying an 85% attainment buffer. That creates optionality: you could push the planned hire out to ~June to manage budget or hire earlier and intentionally lean into overperformance (be sure to confirm AE capacity can absorb the additional pipeline!).

Once everything is layered in, the model is ready to go…explaining it is a different story, and I wish you the best of luck. 😂

🤝🏼 Planning Beyond Revenue Roles

Early on, most teams focus capacity planning on AEs, AMs, and BDRs. That’s normal, and what we did in the early days of SupplyPike. When you’re building the engine, the goal is to generate revenue.

As the business grows, revenue stops being a single-threaded problem. Supporting roles become essential to keeping the system running smoothly and to protect execution. Here are a few key roles to start thinking about as your business grows…

• Customer Success Managers (CSMs) are planned to capacity, not quota. The goal isn’t to maximize revenue per CSM, but to ensure each customer receives the right level of support. Lower-touch accounts can be managed at higher ratios, while enterprise and strategic customers require significantly more time and attention.

• Sales Engineers are constrained by time and level of involvement. Capacity planning starts with clear expectations: how often they join calls, how deeply they support deals, and which opportunities truly require specialist involvement. Once those expectations are clear, you can back into how many sellers one Sales Engineer can realistically support, avoiding both burnout and underutilization.

• Sales and BDR Managers are milestone-driven hires. As a rule of thumb, once you have ~4-5 reps, you should plan to hire your first manager. Managers exist to protect execution through 1:1s, pipeline hygiene, deal strategy, and accountability. If reps are consistently missing expectations or deals feel chaotic late in the quarter, that’s often a signal the team has outgrown its current management layer.

• Sales Ops Analysts become necessary once selling becomes cross-functional and data-dependent. When reps are spending time pulling reports, reconciling numbers across systems, or creating custom analyses for deals, you’re stealing time from selling. A simple rule of thumb: when sellers are maintaining the system instead of using it, you’re late to the game.

🤠 Rounding Us Out: Incentives & Compensation Alignment

With revenue targets, pipeline math, and capacity planning in place, the final step is aligning incentives with the plan you’ve built.

In Part 4, we’ll focus on incentives and compensation and discuss how to design comp plans that reinforce your assumptions instead of working against them. We’ll cover how to think about quotas, accelerators, and payout mechanics in a way that scales with growth, stays aligned with Finance, and avoids expensive surprises.

See ya in Part 🍀!
Stacy

📚 Stacy’s Book Challenge

This year’s goal is…81. 1 more than last year. 😮‍💨 Follow along as I try to get there.

As of this post, I have (still only) read 3 books. Just…don’t judge me, okay?? I’m reading really long books. 😭

I’m currently reading:

• East of Eden - about 75% through now!

• The Will of the Many - about 33% through now!

Follow me on GoodReads! 🤓

Once you’ve locked in your ARR targets by team (and if you haven’t yet, what are you doing?! Go check out Part 1 of this series!), the next question is inevitable:

Where does the revenue actually come from?

Pipeline planning is the bridge between where you’re hoping to land and how you can actually get there. It lays the groundwork for tangible numbers that your team can rally around. Done well, it turns revenue goals into clear demo targets, channel plans, and shared ownership across the GTM organization, and most importantly, it gives your team confidence that there is a path to hitting their goals.

Let’s get into it.

☎️ Translating Revenue into Demos

Every company defines its funnel a little differently, but in B2B SaaS, there’s usually a moment that kicks off the sales cycle. For SupplyPike, that moment was when we showed a demo of our product.

The demo was our clearest signal of real buyer intent and the most reliable predictor of pipeline creation. Your equivalent might be a discovery call, technical evaluation, or trial start - the key is anchoring on the stage that actually moves deals forward.

For simplicity, we’ll use demos as the anchor metric for the rest of this series. Your company may use a different milestone, but the logic holds regardless. Just substitute the stage that best represents meaningful buyer intent in your funnel in the calculations below.

Two key metrics will help you determine how many opportunities you need:

• Conversion rate, which represents the percentage of prospects that move from one funnel stage to the next

  • For this series, we will be focusing on the conversion rate from Demo → Closed-Won, but you can slice and dice conversion rate data at any step of the funnel - we’ll get into this in a future installment of Deal Desk!

• Average Contract Value (ACV), or the average annual revenue generated by a single customer

Step 1: Revenue → Pipeline

Your conversion rate determines how much pipeline you need to hit your revenue target.

Pipeline Needed = Revenue Target ÷ Conversion Rate

In layman’s terms, if 20% of your pipeline closes, you need roughly 5x pipeline to hit plan.

Step 2: Pipeline → Demos

ACV then translates pipeline dollars into the number of demos required.

Demos Needed = Pipeline Needed ÷ ACV

Said another way, if the average Closed-Won deal is worth $10,000, you can back into how many demos it takes to fill, say, a $1,000,000 pipeline.

Together, these determine how many demos are required to support your revenue goals:

Demos Needed = (Revenue Target ÷ Conversion Rate) ÷ ACV

This gives you a clear demo target, which then becomes the foundation for lead planning, channel allocation, and headcount decisions down the line.

At this stage, continue to sanity-check your assumptions. If historical averages are available, they should be your starting point. From there, you can thoughtfully stretch or tighten both conversion rate and ACV goals based on what you know is (or might be) changing.

For example, if you’re launching something customers have been asking for, or your positioning is getting sharper, you can justify being a little more optimistic on conversion. Similarly, if you’re moving upmarket or are planning price increases, it may be reasonable to adjust ACV upward.

Repeat this exercise across any segments or pods that make sense for your business. Taken together, this gives you a clear view of total demo demand across the org.

🧮 Example 1: Let’s Do Some Math

Building on the example we had in Part 1, let’s calculate demo targets for the Enterprise team with a $360K revenue goal.

Assumptions:

• Revenue Target: $360,000

• Conversion Rate: 20%

• ACV: $25,000

Step 1: Calculate Pipeline
$360,000 ÷ 20% = $1,800,000

Step 2: Calculate Demos
$1,800,000 ÷ $25,000 = 72 demos needed

📈 A Note On Pipeline Planning for Upsells

When it comes to upsells, it’s important to note that the math doesn’t change, but the context does.

Upsell planning uses the same framework as New Sales: revenue targets, conversion rates, ACV, and demo volume. The difference is that upsell teams operate within a finite market. Unlike New Sales, you can’t simply source more accounts.

Account Managers and Customer Success Managers are typically constrained by:

• The number of accounts they support

• Where those accounts are in their lifecycle

• The realistic opportunities for expansion

Because of that, upsell pipeline planning requires some additional validation.

We still start by translating upsell revenue targets into demo volume using historical conversion rates and ACV. But before locking those numbers, you should pressure-test them against reality by asking questions like:

• Does this level of expansion make sense given our customer base?

• Are accounts mature enough to support this much upsell activity?

• Is coverage balanced across AMs and CSMs?

This step ensures upsell goals are ambitious without being disconnected from the actual opportunity in the book of business.

💡 Pro-Tip: Demo Scheduled vs. Demo Completed

Not all demos are equal. That was a hard lesson for us to learn. 😮‍💨

In the early SupplyPike days, we planned our pipeline around demos scheduled. That worked when show rates were high. As we scaled, no-shows started to become a real issue. At one point, 30%+ of booked demos didn’t happen. Woof. On paper, our funnel looked healthy. In reality, it wasn’t.

When our conversion rates stopped behaving the way we expected, we shifted to planning and goaling our BDR team around demos completed, which are demos that actually happened, and met our qualification criteria. (Christine actually talked about this in her article on the 5 don’ts of goal-setting!)

Importantly, our BDR team was always compensated for demos completed. But using scheduled demos as the headline metric gave us a misleading leading indicator and masked where the funnel was breaking down. Once we made the switch, our view of pipeline health became far more accurate and far more useful.

🗺️ Lead Source Planning

Once demo targets are set, the next question is where those demos should come from. This is where channels enter the picture.

Most B2B SaaS GTM motions rely on a mix of:

• Outbound (BDR-led prospecting and cold calls/emails)

• Inbound (website traffic, gated content)

• Events & trade shows

• Partners

Channels matter because demand behaves differently depending on where it comes from, and each team contributes to pipeline in its own way. For example, outbound is more controllable but is typically capacity-bound. Inbound compounds over time, but is market-driven. Events can be high intent but lumpy.

The strongest GTM motions are built on a healthy mix of channels working together.

Assigning Demo Targets by Channel

The goal of channel planning isn’t to guess where demand might come from - it’s to intentionally decide where demand should come from.

Sales leaders, this is when alignment really comes into play. Channel goals should never be set in a vacuum - that is a recipe for disaster (ask me how I know 😩). They require close collaboration with leadership across any relevant channels, as those folks can provide you with context around capacity, timing, and constraints. Aligning early helps ensure channel expectations are fair, resourced, shared, and prevents surprises later in the year.

Together, allocate your total demo target across channels using a mix of:

• Historical performance

• Planned investment (budget, headcount, focus)

• What you know is changing in the year ahead

For example:

• 60% of demos from outbound

• 20% from inbound

• 20% from trade shows or events

💡 If you’re early-stage, it’s normal for most demos to come from outbound. That was true for SupplyPike as well. As brand awareness grows, inbound and partner-driven demand typically increase, often improving CAC and efficiency as customers begin to seek you out.

📝 Turning Demo Targets Into Channel Plans

Once demo targets are set by channel, each functional owner should translate those goals into a plan using the levers they control. Sales leaders, you may not own the day-to-day execution, but you should still have visibility into the strategy behind it.

If your org has reliable data, you can even extend pipeline planning above the demo. The idea is the same: once you know how many demos a channel is responsible for, you can work backward to understand the volume required at earlier stages of that channel’s funnel.

For example, if inbound is expected to deliver 50 demos and you know your website converts 5% of its visitors into demos, you’ll need roughly 1,000 visitors to support that goal. From there, Marketing determines how to drive that traffic.

ACV can also add another useful layer. If you’re expecting higher ACV from a specific channel, or historical data shows that certain channels skew Enterprise, that should inform who you target and how. For example, if trade shows have typically yielded higher-dollar deals (and you expect that trend to continue), you can tailor trade show messaging and collateral to better-suit Enterprise prospects.

🧸 Building in Padding (On Purpose)

A common mistake in GTM planning is assuming 100% attainment across the board. A girl can dream.

Alas, in reality, that’s not how sales teams usually perform, and planning that way actually means the business only hits its number if everyone is perfect. In fact, if everyone is hitting (or exceeding) 100% of your number, you may actually have set your goals too low. 👀

A more realistic assumption (and a common industry standard) is planning around ~85% average attainment.

If you plan around that reality, the math changes slightly. You need to goal above your true target to account for normal variation in performance.

Hedged ARR = ARR Target ÷ Hedged Attainment

For example, if your revenue target is $3M and you’re assuming an 85% attainment for your team:

• Hedged ARR = $3,000,000 ÷ 85%

• Hedged ARR = $3,529,412

This is the number you should goal your team to.

How much you overgoal should reflect the maturity of your GTM motion, confidence in your funnel and channel assumptions, historical attainment patterns, and, honestly, your tolerance for risk. 👀 Early on (or if things feel a little unpredictable), more padding is your friend. As things start to settle, you can start to pull that back on the hedge. (Psst - in Part 3, we’ll also cover what happens when you hedge too much. Yes - that’s a thing!)

☎️ Up Next: Bridging Top-Down Strategy with Bottoms-Up Execution

With pipeline and channel targets defined, the last step is making sure those numbers turn into something your ICs can actually execute against.

In Part 3, we’ll shift from top-down planning to bottoms-up execution: translating demo and pipeline goals into individual quotas, capacity models, and headcount plans. We’ll cover how to size roles responsibly, account for ramp and coverage, and provide pointers on how to run your plan through real-world constraints.

See ya in Part 3️⃣!
Stacy

📚 Stacy’s Book Challenge

This year’s goal is…81. 1 more than last year. 😮‍💨 Follow along as I try to get there.

As of this post, I have read 3 books - I added True Grit and The Girl Who Played with Fire! True Grit was my first 5-star book of the year (and I don’t give out that many 5-star reviews!). I’ve never watched the movie either, so I really need to get onto that. 🤠

I’m currently reading:

• East of Eden - about halfway now!

• The Will of the Many - why do I keep giving myself 700+ page books 😭

Follow me on GoodReads! 🤓