Episode
What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google)
- Published
- Nov 30, 2025
- Duration seconds
- 5162
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Summary
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. We discuss: 1. Why GTM is becoming more strategically important in the AI era 2. The rise of the GTM engineer 3. A primer on segmentation 4. How to build a sales org that engineers and product teams respect 5. The changing calculus of build vs. buy for go-to-market tools in the AI era 6. Why most customers buy to avoid pain rather than to gain upside — Brought to you by: Datadog —Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lenny Lovable —Build apps by simply chatting with AI: https://lovable.dev/ Stripe —Helping companies of all sizes grow revenue: https://stripe.com/ — Transcript: https://www.lennysnewsletter.com/p/what-the-best-gtm-teams-do-differently — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/179503137/my-biggest-takeaways-from-this-conversation — Where to find Jeanne DeWitt Grosser: • X: https://x.com/jdewitt29 • LinkedIn: https://www.linkedin.com/in/jeannedewitt — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Jeanne DeWitt Grosser (05:26) Defining go-to-market (08:43) The evolution of go-to-market roles (11:23) The rise of the go-to-market engineer (14:21) Implementing AI in sales processes (15:28) Optimizing sales with AI agents (23:47) Defining sales roles: SDRs and AEs (26:04)…