GTM: Why Most Go-To-Market Motions Collapse at Scale, with Jeanne DeWitt Grosser, COO at Vercel
Podcast: The GTMnow PodcastPublished On: Thu Jan 22 2026
Description: Why do so many go-to-market motions fall apart right when a company starts to scale?In this episode of GTMnow, Sophie Buonassisi sits down with Jeanne DeWitt Grosser, former GTM leader at Google and Stripe and now COO at Vercel, to unpack why GTM fragility is one of the most underdiagnosed risks in startups and scaling companies.This is a deep, operator-level conversation about what actually breaks in sales, why AI won’t magically fix it, and how the best teams treat go-to-market like a product that must be designed, tested, and iterated.If you are a founder, operator, or investor navigating growth, this episode will give you clearer mental models for building GTM that actually holds up under pressure.In this episode, we cover:Why most GTM motions fail at scale, even with strong productsWhat it really means to treat go-to-market like a productHow AI changes execution without changing fundamentalsThe rise of the forward deployed engineerWhy “lost on price” is usually a lieWhat great sales reps still do better than anyone in the AI eraHow to think about joining companies “early” without getting timing wrongListen if GTM feels fragile, unpredictable, or overly dependent on heroes.Timestamps00:00 – Introduction01:00 – “Yes is great. No is great. Maybe will kill you.”02:00 – Why go-to-market should be treated like a product04:45 – Designing the experience of being sold to06:30 – Using AI to debug GTM process failures09:00 – Why “lost on price” usually isn’t about price12:00 – What go-to-market engineering actually is16:00 – The rise of the forward deployed engineer20:45 – AI, agents, and what still needs human judgment25:45 – What great sales reps do differently in the AI era29:30 – Why GTM roles are becoming more consultative33:30 – Will there be an AI reckoning?38:00 – What “joining early” really means42:00 – Career lessons from Google, Stripe, and Vercel44:00 – Closing thoughts
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