Lenny's Podcast · November 30, 2025

What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe,

with Jeanne Grosser

Jeanne DeWitt Grosser, former GTM leader at Vercel and Stripe, reveals how world-class go-to-market strategy is evolving for 2026. Learn why the best GTM teams function as revenue-driving R&D extensions, how AI automation is replacing entire SDR teams while maintaining conversion rates, and the critical frameworks for customer segmentation and discovery calls. Discover why 80% of enterprise customers buy to avoid pain rather than gain upside, and how GTM engineers are revolutionizing sales workflows in competitive AI-driven markets.

Featured insight

The rise of go-to-market engineers can automate entire sales workflows - at Vercel, one GTM engineer spent 30% of his time for 6 weeks to replace 10 SDRs with a single agent-managed process while maintaining conversion rates. — Jeanne DeWitt Grosser

Best for: GTM leaders at B2B SaaS companies, Sales VPs scaling technical products, Founders building enterprise go-to-market strategies

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