AI Uncovers True Reasons for Lost Deals, Bypassing Bias
Every quarter, management teams walk into the board meeting with a “Closed Lost Analysis” slide. It typically shows the top 5 reasons deals didn’t close. Pricing. Missing feature. No budget. Chose competitor. The problem? Much of that data is incomplete, biased, or just wrong. It’s filtered through: • Rep interpretation • CRM dropdown hygiene • Internal politics • And hindsight rationalization By the time it reaches the exec team and board, it looks crisp and quantified — but it often lacks truth. One Stage 2 Capital portfolio company, Rally UXR , took a different approach. Instead of relying solely on rep-submitted loss reasons, they used AI to analyze sales call transcripts across won and lost deals. The AI generated structured summaries and identified patterns at scale — without human narrative bias. What they found: The AI created a more objective and comprehensive view of reality — cutting through rep interpretation and CRM noise, and ultimately enabling more substantive, data-driven changes across the organization. And that’s the opportunity for founders. Before your next board meeting, try this: Keep your traditional “Closed Lost Reasons” slide. But add a complementary slide: “Closed Lost Reasons — AI Analysis of Sales Conversations.” Put them side by side. Where do they align? Where do they diverge? What patterns show up when you remove human filtering? You don’t need perfect AI. You need a second, independent lens. Founders win when they challenge their own assumptions — especially the ones that get presented as data. AI isn’t replacing judgment. It’s helping us audit it. Check out the full article on #DearStage2 , penned by Stage 2 Capital partner, Mandy Cole and Stage 2 Capital LP, Juliette Kopecky , here: https://lnkd.in/efj4ZrE3
AI Will Return Sales to Full‑Cycle Sellers
In the 80s and 90s, most sales reps were full-cycle. They found their own meetings. They ran the process. They renewed and expanded accounts. Then we specialized: --> SDRs (thanks to the “predictable revenue” era) --> CSMs and post-sale roles...
Momentum.io Showcases Enterprise AI's True Work System
Congratulations to Santiago Suarez Ordoñez , Ashley Wilson , Moiz Virani , and the entire Momentum.io team. It’s been a privilege to support you on this journey. Momentum embodied several themes we consistently look for in native AI companies: -->...
Listen First: Buyer‑Centric Sales Beat Product‑Centric Scripts
Most sales processes are built backwards. They are product-centric (inside-out), not buyer-centric (outside-in). And yet, almost every research study shows that top-performing sellers listen more than they talk on the first call. Bottom performers do the opposite. A product-centric sales...
AI Will Shift Sales to 80% Selling Time by 2026
As the AI era evolves, one of the most difficult aspects of predictions is how quickly humans will be abstracted away from today’s “point of work.” Take something as simple as building a toy. The first level of abstraction is...
Startups Should Ditch Annual Plans for Quarterly Reset
Annual planning is one of the most over-copied “big company” rituals in startups—and it quietly creates a lot of bad decisions. In large companies, annual planning makes sense. They’re hiring hundreds (sometimes thousands) of people, mobilizing new strategies, changing systems,...
AI Turns First Sales Hire Into Pure Discovery Role
Nailing the first sales hire has historically been one of the biggest hurdles in kicking off the scaling process. They’re a unique breed: half Account Executive, spending all week in conversations with prospective customers, and half Product Manager, distilling those...
Honest Board Management Beats Optimistic Theater
Here are a few take-aways from the early days of scaling at Okta with their co-founder, Frederic Kerrest . 1. Managing the board: Demonstrated control over the business versus optimistic theater Early in my career, I thought my job with...
AI-Native B2B Apps Are Redefining the Software Landscape
Will B2B software survive the AI era? The last platform shift, on-prem to cloud, created a wave of new category winners. Salesforce, Workday, NetSuite, HubSpot, and GitHub were all native-cloud companies. But the signals are different this time. Foundational models...
Harvard Classroom Refines My Scaling Framework, Benefits All
Teaching at Harvard Business School has been one of the toughest and most rewarding experiences of my career. I’ve been in some tricky startup boardrooms before, but the rigor it takes to work with HBS students is next level. When...
Three Hours Coaching Boosts Sales Attainment Above 100%
The data is clear: teams receiving 3+ hours of coaching per rep per month consistently outperform (thanks Gartner for the analysis). But most teams never get out of reactive mode. “I wish I had more time to coach my reps....
Board Pressure Fuels Unsustainable Product Overreach
The Second Act Stumble Steve had a way of making growth sound inevitable. He’d done it once already—tripled revenue from $7 million to $21 million in 12 short months—and the board wanted another lap around the track. Another 3×. Another...
Teach Reps Buyer‑centricity by Walking in Buyers’ Shoes
One of the most important lessons from our early days building the HubSpot sales team is to teach your reps to start with a buyer-centric mindset. We trained our reps by having them walk in the buyer’s shoes. Every new...
Break‑up Emails: Elite Reps’ Secret to Faster Funnels
What you’re selling isn’t right for everyone. That’s why great sales reps aren’t afraid of break-up emails. They know when it’s time to lean in and when to qualify out. And in a scaling motion, that discipline matters more than...
Automation Isn't AI: Clarify Value Before Overhyping
Lately, I’ve noticed many founders and operators confusing process automation with AI. And honestly, I get why. Boards are pushing executive teams to “integrate AI” into their products and operations. The hunt for efficiency begins. Some of those opportunities lead...
Define Product-Market Fit with Real‑Time Metrics
Is product market fit… a feeling? I’d argue the opposite. PMF shouldn’t be based on intuition. It should be easily defined, and it’s something you can outline early in your sales process. In The Science of Scaling, I share a...
Customer Interviews Mirror First Sales Meetings
In this episode of #TheScienceOfScaling , I sat down with Mike Gamson #FoundingCRO at LinkedIn. We travel back to the early days when LinkedIn clearly had product-market-fit for its members, and Mike had the difficult challenge of devising the commercialization...
Standardize PIPs to Preserve Culture While Removing Underperformers
As founders enter the scale stage, there is a lot of talk about on-boarding talent, but very little talk about off-boarding talent. When scaling a sales team, if you get the new hires right 90% of the time, you are...
Qualify for Success, Not Just a Signature
A common gap in the founder selling playbook: the Customer Success Qualifying Matrix. Most people know the Sales Qualifying Matrix—the framework that helps predict whether a prospect will buy. Common examples are BANT, MEDDIC, and SPICED. This Sales Qualifying Matrix...
Sales Success Starts with Empathy, Alignment, and User‑First Focus
Revisiting a favorite Science of Scaling podcast episode with Aliisa Rosenthal (Founding Sales Leader at OpenAI). Cool stories and learnings from the launch of one of the most important techs in history: 1) During her interview, Sam Altman was concerned...
Scale Revenue Only When Customer Success Is Predictable
If you’re looking for your moment to scale, be careful not to confuse consistent revenue creation with consistent customer success creation. They’re not the same thing. You can grow revenue fast without seeing customer success — especially in the early...
Scale Revenue by Targeting the Right Customers First
I asked 100 successful sales leaders why startups fail to scale revenue. Their answer? It was not because the product is bad. They stall because they’re growing on the backs of the wrong customers. In this The Science of Scaling...
Daily Film Review Drives Scaling and AE Self‑Sourcing
In a recent episode of #TheScienceOfScaling , I interview Ron Gabrisko , the Founding #CRO of Databricks . He has scaled Databricks over a nine-year period (so far) from essentially $0 to $2.5 billion in ARR. Here are a few...
From Small‑Town Labs to $12M Seed: AI Startup Soars
“Cyber Agent Closes $12M Seed Round from Big VC” Doug couldn't believe it. His company—his dream, his obsession—had just raised more than $12 million on a $60 million valuation. Doug was now a multimillionaire, at least on paper. Doug leaned...
Scaling Learning, Not Headcount, Drives Sales Success
Most sales teams don’t have a pipeline problem. They have a learning problem. The symptoms are the same everywhere: Higher costs. Flat quota attainment. Exhausted reps wondering why “work harder” is somehow still a strategy today. Meanwhile, the top-performing teams...
Validate PMF with Retention Before Scaling Sales Hires
I keep hearing the same story: A founder raises a $15M Series A. A board member says, “Hire 20 reps in November.” A few months later… all 20 are gone. It still happens, far more often than we like to...
AI Startups Should Prioritize Upmarket Strategy over Quick Downmarket Wins
Last week, we brought together more than 325 founders, LPs, and go-to-market leaders at Google NYC HQ for the Stage 2 Capital Summit. It continues to be my favorite day of the year, as I get a front-row seat to...
Stop Treating AI as Magic—Build the Right Architecture
The “AI black box” is killing momentum in GTM teams. And it’s no longer just a technical challenge, it’s an architecture problem. That’s the idea I explored in Chapter 2 of Ignite Your GTM with AI, a project brought to...
AI Coach Turns Prospecting Into Real‑Time Sales Wins
March 15, 2026. San Francisco, CA Sara had finally booked the meeting. A conversation with the Director of Marketing at a major pharmaceutical company. It had taken six weeks of disciplined prospecting to get there. A long night of preparation...
AI Will Boost Selling Time to 80% by 2026
Most GTM teams haven’t even entered Phase 1. That’s the punchline of this new piece I wrote regarding my hypothesis on how AI will reshape field of go-to-market over the next decade. In the work, I propose four sequential phases...
AI Is Redefining Buyer Behavior—GTM Must Evolve
Congrats to the Topline team on their launch of Topline Media! AI is reshaping buyer behavior. GTM needs to keep up. I’ll be sharing a few perspectives in an upcoming post, but also looking forward to learning from others in...