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What World-Class GTM
Looks Like in 2026

Jeanne DeWitt Grosser
COO, Vercel; former Chief Product Officer, Stripe
NOV 30 2025
The Thesis

GTM Got Consultative,
Then It Got Coded

GTM LEVERAGE
"If you are an account executive in my org and I put you in front of 10 engineers at our company, it should take them 10 minutes to figure out you aren't a product manager."
  • Consumption-based models pushed GTM from transactional to consultative
  • The go-to-market engineer emerged in the last 18 to 24 months
  • Sellers historically spend 30 to 40% of time with customers; the aim is 70%
Framework

How Jeanne Turns a
Workflow Into an Agent

SHADOWENCODEHUMAN QA
10 → 1
Vercel's inbound SDR function collapsed from 10 people to 1 QA-ing the agent; the other 9 moved to outbound. Lead agent runs for about $1,000 a year.
  • Step 1: Shadow the highest-performing human in that function
  • Step 2: Encode the workflow, deterministic where you can, agent where you can't
  • Step 3: Let the agent draft; a human reviewer hits send
  • Step 4: Track lead-to-opportunity conversion, number of touches, time to convert
The Stripe precedentProject Rosland at Stripe (2017) tried to build a "company universe" for targeted outbound. It didn't work then. With AI, Jeanne says the same idea works now, and Vercel is rebuilding it.
The New Enterprise GTM

Jeanne's Lessons From Stripe to Vercel

  • Sell like a product: "How do you make it be an experience rather than a transaction?"
  • Discovery over pitch: "Excellent salespeople typically will talk well under half the time."
  • Signal over spray: For install-based sales, product usage tells you the next best action
  • Feed the roadmap: A 20-person sales team talks to more customers a week than most PM orgs
The whiteboarding first call

At Stripe, the first call after qualification was a whiteboarding session, not a discovery quiz. Customers drew their own payments architecture and left with an asset.

The dogfood advantage

Vercel's GTM builds every internal agent on Vercel's own AI cloud, AI gateway, workflow SDK, fluid compute. The team is customer zero for the product it sells.

Playbook

Build World-Class GTM

  • Hire your first salesperson around $1M ARR, once your ICP is repeatable
  • Bring revenue operations in earlier than you think, it gives you the data to see what's working
  • Segment on about three attributes, more than three is over-cutting
  • Add value at every touch, even for prospects who don't buy this cycle
  • Kill freemium if it isn't earning its keep, Stripe Billing did it with zero downside
Jeanne's 80/20"80% of customers buy to avoid pain or reduce risk," not to chase upside. Frame the risk they're taking by not moving.
Contrarian

GTM Takes From Jeanne

✗PLG alone will scale youINSTEAD →✓ "People are generally not going to give you $1 million via self-serve flow." PLG has a ceiling; every company eventually adds sales.
✗Lead with the vision and the upsideINSTEAD →✓ "80% of customers buy to avoid pain or reduce risk." Frame the risk of not moving, not the art of the possible.
✗AI will replace all SDRsINSTEAD →✓ AI takes the rote work. At Vercel, 9 of 10 inbound SDRs moved up to outbound; 1 stayed to QA the agent. Deep enterprise prospecting still needs humans.
✗Every product needs a freemium tierINSTEAD →✓ Stripe Billing killed its free trial "to zero downside." Freemium without a strategy is a leak.
Based on Jeanne DeWitt Grosser's episode on Lenny's Podcast. All ideas on this page are from the episode.Watch on YouTubeFollow @jdewitt29 on X
GO DEEPER IN THE EPISODE
05:26 Defining go-to-market08:43 The evolution of go-to-market roles11:23 The rise of the go-to-market engineer14:21 Implementing AI in sales processes15:28 Optimizing sales with AI agents23:47 Defining sales roles: SDRs and AEs26:04 When to hire a GTM engineer29:04 Hiring and scaling sales teams30:50 The ideal go-to-market engineer34:24 The go-to-market tool stack40:39 Advice on building a great sales bot44:34 Vercel’s unfair advantage46:37 Go-to-market as a product47:04 Innovative sales tactics at Stripe52:38 Effective go-to-market tactics01:00:37 Segmentation strategies01:09:31 Building a sales org that engineers love01:14:00 Thoughts on PLG and pricing01:16:44 Sales compensation and hiring01:19:24 Lightning round and final thoughts
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