Leah Chapman

Salesloft and Clari announced a merger. I call it a surrender. The legacy SaaS Unicorns are dying. Creative mergers and cap table restructuring is what happens when you burn through $937m in venture money and cannot grow sustainably. The VCs are paying for their mistakes. Employees equity will be crushed. Welcome to the new era of SaaS Wealth Destruction. But don’t worry, there’s a silver lining on the other side … BACKGROUND: When Salesloft acquired Drift in early 2024, I wrote: “To me, this is a merger that marks the beginning of many such mergers across all VC and PE portfolios that will play out in the next 1-2 years.” The Clari + Salesloft merger is another signal that the current winner take all investment and operating model no longer works. Over-capitalization no longer justifies premium pricing. The biggest and loudest conference booths no longer guarantee margins. The game has changed. Expect few years of “Creative Mergers” just to survive what’s coming.  Let’s first review the merged company: Drift + Salesloft + Clari + 9 other smaller acquisitions raised a total of $937M in venture funding and at its peak it had a combined valuation of $6.2 billion. Since the cap table was restructured with this merger; Clari’s real valuation is likely far lower - meaning investors and employees on both sides took a big hit. This is both a warning shot and a beginning of what’s coming. AI is going to accelerate such creative mergers and associated SaaS wealth destruction. Many Unicorns have to undergo this process to stay relevant or slowly fail. Ironically, the smartest Unicorn founders will choose valuation-crushing deals & rush to merge with other Unicorns. While such mergers destroy wealth and indicative of surrender, they are healthy for the overall ecosystem moving forward. Roughly 350 unicorns raised capital in the last 5 years. Many need restructuring. Why Salesloft + Clari merger make sense for the future? The real battleground of the future is CAC. CAC has already exploded in the past few years (60% for large SaaS). A platform like Salesloft + Clari has the potential  to subsidize CAC across multiple solutions and platforms while premium end point solutions will find it hard to survive and justify the ever rising CAC. Buyers are moving away from “Best of Breed” to “All in One” platform purchases. This also helps with the rising CAC. Every vertical will see the rise of multiple MEGA platforms - often a result of combining multiple Unicorns. With Clari + Salesloft’s combined product portfolio, data exhaust and high-quality customer base, Clari has a good shot at positioning itself as one of the MEGA revenue platform of the future. I hope more Unicorn founders have the courage to admit their mistakes and restructure before the music stops. But in the meantime, buckle up and get ready. We will see many more deals like this in the next 12-18 months. Welcome to the era of SaaS Wealth Destruction.

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I’ve run many deal reviews over the last few weeks. Three of the deals were “stuck.” My advice for “unsticking” each was the same: “Make the next step easier for the prospect.” Sellers have to remember: 99% of your prospect’s job is not related to buying your product. 100% of your job is helping them buy your product. So you should do all you can to make every step as easy as possible for your prospect. A common time deals get “stuck” is right before a trial or a proof-of-concept. The most common reason deals get stuck at this stage is sellers wait for the prospect to finalize the trial/POC criteria. Think about all the work this creates for your prospect: - Schedule internal meetings to discuss requirements - Document requirements, and determine outcomes - Circulate document internally to get feedback/sign-off from anyone that missed the meeting(s) Add in vacations/busy schedules and these few steps could easily take weeks. A better route is making the next steps easier for your prospect - here's how we did it for our “stuck” deal: 1) Built our recommended PoC requirements and outcomes I told the AE to review the discovery and demo transcripts to make sure we cover customer mentioned required capabilities and tie to customer stated metrics. Then, I told them to add in additional required capabilities we know they’ll need to be successful, along with the outcomes they drive. Ideally, at least a few of these would be required capabilities we know our competition struggles to provide. 2) Position us as experts + make prospect’s job easier Once our recommended proof-of-concept approach was built, we sent to the prospect with a note: “We’re looking forward to kicking off your proof-of-concept. We’ve done a ton of these so we built out an initial template you can use as you build out your requirements - we made sure to include everything you mentioned as being essential in prior conversations + what we’ve seen necessary for customers with similar goals. Feel free to add/remove from this starting point, but hopefully this saves you some time. How’s your calendar next week to discuss this template + any necessary revisions?” Sure enough, this approach got the prospect engaged again. Take 30 minutes this week to review “stuck” deals in your pipeline. For each deal, write out: - What is the next step the prospect has to take? - What part of it can you do for them? And I bet you see a few “stuck” deals get moving again as you make it easier for your prospects to evaluate your solution. If you found this post helpful, you’ll love the AE Operating System. Templates, scripts, prompts, and more for every part of the deal cycle to help you sell more - the same tactics I've taught my teams to 2x our deal size, increase our win rate, and more than triple the percentage of reps hitting quota. Hundreds have already jumped in - and early feedback has been incredible. If you don't have your access yet, you can join at hitmyquota.com!

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STOP doing what 99% of salespeople do I've helped scale 2 startups to $10M+ ARR... And trained thousands of sales reps across 500+ enterprises. Here's what I've noticed: Most reps are stuck using outdated techniques from 2010. They pitch features ❌ They chase prospects ❌   They wonder why deals fall through ❌ Meanwhile, the top 1% are using these psychological triggers: 𝟭. 𝗧𝗵𝗲 𝗔𝘀𝘀𝘂𝗺𝗽𝘁𝗶𝗼𝗻 𝗖𝗹𝗼𝘀𝗲 Stop asking "Are you interested?" Start saying "When we move forward..." The brain defaults to agreement when presented with inevitability. 𝟮. 𝗦𝘁𝗿𝗮𝘁𝗲𝗴𝗶𝗰 𝗦𝗶𝗹𝗲𝗻𝗰𝗲 After stating your price, shut up. The first person to speak loses. Silence creates psychological pressure that closes deals. 𝟯. 𝗧𝗵𝗲 𝗧𝗮𝗸𝗲𝗮𝘄𝗮𝘆 "This might not be right for you..." triggers loss aversion. People want what they can't have. Use scarcity as your secret weapon. 𝟰. 𝗦𝗼𝗰𝗶𝗮𝗹 𝗣𝗿𝗼𝗼𝗳 𝗦𝘁𝗮𝗰𝗸𝗶𝗻𝗴 Don't just say "other clients love this." Say "3 Fortune 500 CEOs told me this exact solution saved them $2M last quarter." Specificity sells. 𝟱. 𝗧𝗵𝗲 𝗙𝘂𝘁𝘂𝗿𝗲 𝗣𝗮𝗰𝗶𝗻𝗴 "Imagine walking into your office 6 months from now, knowing you solved this problem..." Paint the picture. People buy the future, not the present. The brutal truth? The difference between average and elite isn't talent. It's psychology. Which skill will you try first? ⬇️ ♻️ Repost to help your network and follow Gaurav Bhattacharya for more. P.S. If you're building/leading a revenue team & want early access to our agentic AI that triples pipeline, comment "Agentic".

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Every sales org has a pipeline: Stage 1. Stage 2. Forecast. Commit. You can recite it in your sleep. But when it comes to renewals? Crickets.... There’s no real-time view of customer risk. No weekly trendline. No forward-looking model that projects retention. Isn't that kinda bonkers? You FORECAST growth, but you DISCOVER churn...usually when it’s too late to fix. The big mistake is presuming retention is a lagging indicator, when it would be more accurate to define it as a neglected one. Think about it...most CS dashboards read like a rearview mirror: - Usage metrics. - Ticket volume. - NPS. Useful? Sure. Predictive? Nah. Because churn doesn’t start when a customer says they’re leaving. It starts months earlier when their exec sponsor stops showing up. If you can spot the risk early, you can unlock more levers: - Re-engage power. - Reset the value narrative. - Escalate to commercial. - Offer roadmap visibility. - Re-map success metrics post-reorg. But none of that works if your team can’t see it coming, which is why you need a churn forecast...just like you do for revenue. Build a churn pipeline. Treat it like sales. Some things to build into this: 1. Define churn stages. Just like deals, risk evolves: - Stage 1 (Early): No exec alignment, lagging adoption, stakeholder turnover. - Stage 2 (Mid): Value not realized, weak champion, limited engagement. - Stage 3 (Late): Renewal live, buyer pushing back, pricing/legal blockers. Assign clear criteria. Surface it in Gainsight, CZ, or Salesforce. Manage it like opportunity stages. 2. Assign prevention plays. Each stage should trigger a play: - Stage 1 = exec outreach + roadmap session. - Stage 2 = commercial review + value plan. - Stage 3 = C-level call + tailored retention offer. Codify this. Don’t let reps improvise. 3. Forecast it weekly. Revenue leaders inspect pipeline weekly. CS should do the same with churn. Ask: - How many accounts moved stages? - What’s projected retention by segment? - What % of at-risk logos have exec visibility? Also, share your churn forecast with the CFO. If the CFO sees new logo pipeline every Monday, but doesn’t see churn risk until Q4? That's no bueno. Start sending a weekly churn report with: - Total ARR at risk. - ARR by churn stage. - Stage progression. - Active recovery plays. - Forecasted retention (with confidence levels). This reduces surprises while also forcing accountability. Why? Because churn is rarely a CS failure, but it's often a product gap, pricing mismatch, or sales promise that aged poorly. When churn is forecasted, it becomes EVERYONE'S problem. Which it is. tl;dr = you don’t “discover” churn. You forecast it. You stage it. You act on it. Just like sales.

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Here’s why high-performing sales reps leave. They hit quota. They lift the whole team. They make the company money. And their reward? A punishment. Next year’s quota goes up. Targets get “stretched.” The goalposts move. It’s like telling a marathon runner, “Great job on 26 miles, next year, it’s 35.” High performers don’t burn out from selling. They burn out from feeling like success just makes the hill steeper. Want to keep them? Reward them with ownership. More stock. Autonomy. More money. A Rolex (if that’s there thing.) Not a bigger rock to push uphill.

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How to turn your AEs into a winning team: - product positioning - Discovery training - Command of the message - Great CRM setup - Nice Sales deck - listen to Calls in Gong ^^ tasks split across marketing, RevOps, AE leader, enablement. How to turn your SDRs into a winning team: - map the TAM - learn a variety of decision maker titles - cold calling training - set up email infrastructure - buy and set up multiple data tools - learn copywriting for exec communication - learn about SMTP, DMARC, DKIM - run complex math to determine how many leads are needed - collaborate with marketing for MQL handoff - optimize sequence settings to prevent bottlenecks - validate CRM data to prevent bounce leads - learn LinkedIn strategy for messaging prospects - learn to leave proper voicemails - run discovery on inbound leads - build a variety of sequences - run the math on A/B testing messaging - pass proper notes to the AE - follow up with leads that ghosted the AE - handle phone objections different than email ones - test a variety of tools, and fight for budget contstantly - help SDRs career plan and understand comp plan ^^ worst of all, the SDR manager has to do 90% of this in their own! Then SDRs and SDR leaders are paid less than their AE counterparts. Then when things aren’t working the SDR team is cut while the AE team is trained. How does this make sense? Been saying it for years #SDRsMatter

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If I was a founding AE tasked with closing the first $1M in revenue… I wouldn't cold call/cold email until my face melted Here’s the approach I’d run instead ⬇️ 1️⃣ Laser ICP focus Who does my product have the most value for? What persona does this pain resonate with? Who do I have the product TODAY to serve. 2️⃣ Outbound with Flare No spray-and-pray. Every touch would prove I understand their business and how my value serves them better than the last 5 reps who pitched them. 3️⃣ System > heroics Every email, objection, and win gets documented. The goal isn’t just closing deals - it’s creating a machine others can run based off your experience. 4️⃣ Anchor with Trust Not just revenue. Early wins have to validate the product and your champions turn into sales people, they validate their wins and provide trust that start-ups desperately need. Because here’s the truth: 👉 The first $1M is a proof of concept to what is repeatable. 👉 It’s the signal that drives the next $10M. What would you add to this list?

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Too much sales outbounding still starts with the same lines:  ☑️ “Just checking in.”  ☑️ “Hope you're doing well.”  ☑️ “We help companies like yours…” The future of selling is rooted in real connection, not automation. Every touchpoint is a chance to differentiate or disappear. Personalization is more than using a name or company, it’s about showing you’ve done the work to understand what matters. That’s how conversations start. Sellers win when they treat outreach as a conversation, not a template. Revenue is a team sport — and that starts with every seller showing up with empathy, insight, and intent. Let’s raise the bar. The buyer deserves it. So does your pipeline.

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Please, for the love of revenue, stop opening your pricing call by pulling up the proposal and running through the price. You’re not a waiter dropping the check at the table. If the prospect says, “We just want to review the price,” that’s your signal to slow down and give context to the conversation. Every pricing call should start by confirming: - current challenges or problems to be solved - desired outcome for their business - how your product or service is going to deliver the outcome for them Once you are aligned on these three things, you can move forward with showing the price. This is especially important when a new evaluator joins the call. For example, you have been working with a champion who gets to the point where they want to see the price. You schedule the call to review the commercial terms. They invite the CFO or the economic buyer. That CFO has no context for value that you are going to deliver. They haven’t felt the pain you’ve been unpacking over the last few weeks. That's your job to give them the right context. Price only makes sense when you understand the current challenges and desired outcomes. That’s why I always start pricing calls the same way: “Before we jump into numbers, I just want to make sure we’re aligned on the goals of this partnership. Can we quickly revisit the challenges you’re solving and the outcomes you’re targeting? I want to make sure the proposal maps to that.” It’s a hard thing to say no to. And it does two important things: It gives you a chance to reinforce the value. It opens the door for new information or things the buyer hasn’t told you yet, but that will matter in the decision. I have lost many sales opportunities in my career by rushing to show the pricing. I thought moving fast meant being efficient. But I skipped the context. So the next time you have a pricing call, slow down. Frame the conversation. Align on the value of the partnership. Then move on to the commercial terms. ______ If you need help structuring that conversation, I’ve got an executive summary template that makes this easy. Comment "Summary" and I'll send it to you.

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You know the #1 thing I tell sales reps they need to improve on if they want to be more successful in sales? It's not any specific technique. It's business acumen. If you understand all the different aspects of business, how everything works together, the different roles and KPIs, how people are measured, etc. you become far better at every level of sales including: - Your messaging when it comes to prospecting - Your ability to qualify opportunities in and out - Your understanding of business impact and root cause AND Your ability to negotiate. I dove into this and much more with Giuseppe Conti on this week's episode of the Make it Happen Monday podcast. How else do you see business acumen impacting your ability to sell?

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