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

Stop Letting Ballparks Become the Budget

Modern Craftsman

Outro

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