Lenny's Podcast: Product | Career | Growth
What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google)
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I've been getting so many asks for go-to-market help. With AI, it's just intensified because you have 10 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. The 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 going to enable in the future, but that's often really a sale that's going to resonate with another founder. Everybody else, particularly enterprises, you're avoiding the risk of not making your revenue target 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 you're superpowers 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 10 engineers at our company, it should take them 10 minutes to figure out you aren't a product manager. Today my guest is Jean Grocer. Jean was Chief Business Officer at Stripe where she built her very early sales team from the ground up. She's currently COO at Verssell 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 Shafer 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 of a ton of incredible products, including Devin Lovable, Replied Bolt, N8 and Linear Superhuman Descriptless Proflogama perplexity, warp good and all the magic patterns, raycat, shape, air, D, mob and hand, stripe, atlas, head on over to lenniesnewsletter.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 Data Dog, now home to Epo, the leading experimentation and feature flagging platform. Product managers at the world's best companies use Data Dog. 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, Data Dog goes even further. It helps you actually diagnose the impact of funnel drop-offs and bugs and UX friction.
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