Lessons from Vercel’s COO
As an operator who scaled both Google and Stripe for a decade each before joining Vercel, Jeanne Dewitt-Grosser’s insights
bridge the gap between “traditional” best practices and the future of “vibe-coding” and AI agents.
After sitting down with Jeanne to unpack her scaling philosophy, we’ve distilled four core lessons:
Lesson 1: Treat go-to-market as a product.
Lesson 2: Hire go-to-market engineering early.
Lesson 3: Solve for “maybe” (the silent deal killer).
Lesson 4: Use these three considerations for picking winning companies to work at
Below, we dive into each lesson. This is the fourth part of a new series on lessons from some of the top 1% leaders in B2B SaaS.
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Lesson 1: Treat go-to-market as a product
When teams build software, they prototype 10+ versions of a screen and debate 10 pixels of spacing. Jeanne argues that sales deserves the same level of intention. GTM isn’t something that should “emerge,” it should be designed with intention.
You’re selling a product – yes – but you’re also designing the experience of being sold to. Every moment matters. The digital ad, the first call, the whiteboarding session, the deck, the follow-up email… each touchpoint should be intentional, sequenced, and story-boxed the way a product team would wireframe a user flow.
Treating GTM like a product also forces clarity. You’re defining what great actually looks like, making the process legible.
That legibility is what unlocks the next wave of automation. If you want AI agents to run parts of your go-to-market, you first need a clear point of view on what excellence looks like.
Lesson 2: Hire go-to-market engineering early
Jeanne is also one of the earliest adopters of what has now become the GTM engineering function.
Traditional RevOps is largely about managing third-party systems (think Salesforce, dashboards, routing rules, etc.). GTM engineering flips that model. Instead of buying more software, you build first-party systems designed specifically for how your team actually sells.
At Vercel, this was one of Jeanne’s first hires. And it changed how the entire GTM org operates.
Rather than adding more SaaS, they build internal agents. “For example, “D0” agents let anyone ask complex data science questions in plain English and get real answers.
Vercel has a joke that they only want to employ 1,024 people (a “kilobyte” of staff). By using GTM engineering and AI agents to handle the “deterministic” parts of the job, Jeanne aims to move her entire organization up Maslow’s Hierarchy of Needs. The goal is to free humans to do the high-trust, high-relationship work that machines can’t touch.
Lesson 3: Solve for “maybe” (the silent deal killer)
Clarity is the only real currency in sales. As Jeanne says: “Yes is great. No is great. Maybe will kill you.”
Early reps and founders tend to fear the no, but a fast no saves the most precious resource an operator has: time.
The real enemy is the maybe. And to eliminate it, Jeanne uses AI to get to ground truth.
She built what she calls the Lost Bot. Most reps misdiagnose why deals fall apart, defaulting to “price” because it’s the easiest box to check in a CRM. The Lost Bot goes deeper. It reads every email, Slack thread, and Gong call to surface the actual source of friction.
In one case, a deal logged as a price loss wasn’t about price at all. The buyer was never the economic decision-maker. That insight changed the response entirely, from discounting to coaching reps on executive selling.
That clarity tells you what to fix and what not to waste time on.
Lesson 4: Use these three considerations for picking winning companies to work at
Jeanne’s career path – Google to Stripe to Vercel – follows a very deliberate pattern. She consistently chooses companies operating in the 99.9th percentile, and her filter is firmly anchored on the invention side of the spectrum.
She looks for teams that hire true inventor engineers. These are the people building the open-source foundations and core models the rest of the industry will eventually build on top of.
She also avoids companies that are really just features. Instead, she looks for horizontal platforms with natural expansion paths. Stripe didn’t stop at credit cards; it moved into fraud, identity, and finance infrastructure. Vercel didn’t stop at front-end tooling; it expanded into AI. The pattern is platform first, adjacencies second.
And then there are values. Jeanne avoids companies where values live on posters and onboarding decks. At Vercel, values are operational. They shape everything, from all-hands agendas to performance reviews.
A combination of those those three elements is how she picks winners:
- Deep invention
- Platform leverage
- Values that actually govern behavior
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- SaaStr Annual: May 12-14, 2026 (San Francisco, CA)
- GTMfund AGM + Retreat: May 14-16, 2026 (San Francisco, CA)
- INBOUND: September 16-18, 2026 (Boston, MA)
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- GTMfund dinner schedule coming soon!
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