Why Most Go-To-Market Motions Collapse at Scale, with Jeanne DeWitt Grosser, COO at Vercel

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 products • What it really means to treat go-to-market like a product • How AI changes execution without changing fundamentals • The rise of the forward deployed engineer • Why “lost on price” is usually a lie • What great sales reps still do better than anyone in the AI era • How to think about joining companies “early” without getting timing wrong Listen if GTM feels fragile, unpredictable, or overly dependent on heroes. Timestamps 00:00 – Introduction 01:00 – “Yes is great. No is great. Maybe will kill you.” 02:00 – Why go-to-market should be treated like a product 04:45 – Designing the experience of being sold to 06:30 – Using AI to debug GTM process failures 09:00 – Why “lost on price” usually isn’t about price 12:00 – What go-to-market engineering actually is 16:00 – The rise of the forward deployed engineer 20:45 – AI, agents, and what still needs human judgment 25:45 – What great sales reps do differently in the AI era 29:30 – Why GTM roles are becoming more consultative 33:30 – Will there be an AI reckoning? 38:00 – What “joining early” really means 42:00 – Career lessons from Google, Stripe, and Vercel 44:00 – Closing thoughts