What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google)
episodePreviously titled “The future of AI-powered sales with Vercel COO, Jeanne DeWitt” — renamed by the publisher on Aug 2, 2026
Transcript
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What is go‑to‑market (GTM) and why is it becoming more strategic in the AI era?
I've been getting so many asks for go to market help.
With AI it's just intensified because you have ten players pursuing the same market opportunity. And so your ability to actually bring the product to market, to differentiate yourself from the competition has become more strategically important than it was previously.
Jenna Abel on the podcast recently. One of her tips is you don't want to be focusing on here's the pain and problem we're solving, and instead focus on here's how you will be better than your competitors.
80% of customers buy to avoid pain or reduce risk as opposed to increase upside, which is a good thing for startup founders to understand. We all love to talk about the art of the possible, everything we're gonna enable in the future, but that's often really a sale that's gonna resonate with another founder or everybody else, particularly enterprises. You're avoiding the risk of not making your revenue target next. Next quarter.
I've heard a lot about how you think about go to market as a product.
We buy a lot of things because of how we feel about them. 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 the margin. And so then you really want to create a customer buying journey that feels like very unique experiences.
Something I've heard from so many people you've worked with is that your superpower is building a sales org that doesn't feel like a sales org to engineers. 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 front of ten engineers at our company, it should take them ten minutes to figure out you aren't a product manager.
Today, my guest is Jean Grosser. Jean was Chief Business Officer at Stripe, where she built their very early sales team from the ground up. She's currently COO at Vercell, where she oversees marketing, sales, customer success, revenue ops, and field engineering. Jean has built world class go to market teams at multiple unicorns and has advised dozens of companies on doing the same. In our conversation, we go deep on what a world class go to market team. Looks like, including what the heck is go-to-market, the rise of the go-to-market engineer, and how this role is already enabling her team to operate 10 times faster, a bunch of very specific tactics to level up your go-to-market skills, a primer on segmentation, how to think about your go-to-market process like a product, her favorite go-to-market tools, her hot takes on PLG and sales comp and sales hiring, and so much more.
If you are looking to get smart on the latest and greatest in go-to-market thinking, this episode is for you. A huge thank you to Claire Hughes-Johnson, Kate Jensen, and James Diet for suggesting topics for this conversation, and Kelly Schaefer for the connection. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It helps tremendously. And if you become an annual subscriber of my newsletter, you get an entire year free. Free of a ton of incredible products, including Devin, Lovable, RapLid, Bold, NADN, Linear, Superhuman, D Script, Whisperflow, Gamma, Perplexity, Warp, Grenola, Magic Patterns, Raycatch JPR, D Mob, and Hand Stripe Atlas. Head on over to Lenny's Newsletter.com and click Product Pass.
With that, I bring you Gene Grosser after a short word from our sponsors. This episode is brought to you by Datadog, now home to EPO, the leading experimentation and feature flagging platform. Product managers at the world's best companies use Datadog, the same platform their engineers rely on every day, to connect product insights to product issues like bugs, UX friction, and business impact. It starts with product analytics, where PMs can watch replays, review funnels, dive into retention, and explore their. Growth metrics. Where other tools stop, Datadog goes even further. It helps you actually diagnose the impact of funnel drop-offs and bugs and UX friction.
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Chapters
8 chapters
1
What is go‑to‑market (GTM) and why is it becoming more strategic in the AI era?
0:00–10:40
2
How has the role of the go‑to‑market engineer emerged and what impact does it have on sales speed?
10:40–21:50
3
What are the core principles of effective segmentation for GTM teams?
21:50–32:38
4
How can a sales organization be built so that engineers and product teams love working with it?
32:38–44:30
5
When should a company choose to build its own GTM tools versus buying existing solutions?
44:30–57:55
6
Why do most customers buy to avoid pain rather than to gain upside, and how should GTM messaging reflect that?
57:55–1:08:33
7
What pricing and PLG (product‑led growth) strategies work best for SaaS companies today?
1:08:33–1:21:13
8
What final advice does Jeanne share for sales compensation, hiring, and staying competitive?
1:21:13–1:25:58
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