Lenny’s Podcast · Podcast episode · Go-to-market & sales · Building AI products

What world-class GTM looks like in 2026

Lenny Rachitskywith Jeanne GrosserNov 30, 2025100 min▶ 132K
SourceLenny’s Podcast
KindPodcast episode
PublishedNov 30, 2025
Readers▶ 132K
Originalyoutube.com ↗
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Jeanne Grosser, COO at Vercel and former Chief Product Officer at Stripe where she helped build early sales teams, discusses what a world-class go-to-market (GTM) function looks like today. The conversation covers the rise of the GTM engineer and AI-driven sales workflows, customer segmentation, treating go-to-market as a product, PLG versus sales-led growth, pricing, and sales hiring and compensation.

01Key learnings

  • Treat go-to-market as an integrated lifecycle spanning marketing, sales, customer success, and support, mapping the jobs to be done from first awareness through long-term retention.
  • Expect the buyer experience of being sold to to become a differentiator, so design the sales journey as a distinctive, valuable experience rather than a transactional pitch.
  • Frame value around avoiding pain and reducing risk, since many buyers purchase to avoid downside rather than chase upside, especially enterprises.
  • Hire a go-to-market engineer who understands sales craft, then have them encode your best human workflows into agents with a human in the loop; Jeanne's team cut an SDR team from ten to one this way.
  • Use conversation analysis tools like Gong with agents to diagnose lost deals and coaching gaps, then run weekly sprints to fix go-to-market process bugs.
  • Build segmentation on a few attributes (around three) such as company size, growth potential, and workload type, then use data to find which traits correlate with revenue.
  • Add value at every touchpoint, even for prospects who do not buy, by offering insights and best-practice content, since lost customers often return years later.
  • Make the sales org feel like a partner to product and engineering by having reps deeply understand the product so they can separate real market signal from noise.
“The litmus test I have always given my sales team is if you are an account executive in my org and I put you in…”Jeanne DeWitt Grosser · Lenny’s Podcast · 01:09:59
“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…”Jeanne DeWitt Grosser · Lenny’s Podcast · 00:48:01
“Yeses are great, nos are great, maybes will kill you.”Jeanne DeWitt Grosser · Lenny’s Podcast · 01:25:25

02Frameworks mentioned

Summary and takeaways written by PM Atlas; quotes are short excerpts. © the original author.