Jeanne Grosser
Jeanne DeWitt Grosser built world-class GTM teams at Stripe, Google, and, most recently, Vercel, where she serves as COO and oversees marketing, sales, customer success, revenue operations, and field engineering. She transformed Stripe’s early sales organization from the ground up and advises founders on GTM strategy.
Episode
What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google)
Summary
Jeanne DeWitt Grosser, COO of Vercel and former head of sales at Stripe, delivers a highly tactical enterprise GTM playbook covering customer segmentation, why 80% of enterprise buyers act to avoid risk rather than capture upside, and how to design sales like a product. She shares how Vercel's GTM engineering team built AI agents — replacing a 10-person SDR function for roughly ,000/year.
Key Takeaways
80% of enterprise buyers purchase to avoid pain and reduce risk, not to capture upside. Structure your pitch around what they will lose without your product.
Segment your market on more than company size: layer in growth potential and workload type, then use data to find which attributes predict revenue.
Think of go-to-market as a product: map every customer touchpoint and design each step to feel human and valuable, not transactional.
Build AI agents for your own GTM workflow before buying tooling — Vercel replaced a million-dollar SDR function with one engineer and a ,000/year lead agent.
PLG has a natural ceiling — start building your outbound sales engine earlier than feels necessary because turning outbound predictable takes time you cannot compress.
Notable Quotes
“With AI, it's just intensified because you have 10 players pursuing the same market opportunity and so your ability to actually bring the product to market to differentiate yourself from the competition has become more strategically important than it was previously.”
“We buy a lot of things because of how we feel about them. The experience that you have of being sold to will increasingly actually differentiate a company and drive buying decisions if products are only different at the merchant. And so then you really want to create a customer buying journey that feels like very unique experiences.”
“So I don't know that I have a point of view yet on what's the optimal size and scale, but I forever have given founders the advice that you often want to bring in revenue operations, which is basically the analytical arm of sales earlier than you think because having data, having process is actually what gives you insights as a founder into what is and isn't working. And so I would argue just like it's a good idea to have that sooner than later, increasingly it'll probably be a good idea to have GTM engine and be looking to bring agents to bear on your process at the outset.”