What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google)

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.

I had Jen 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 increased 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. For 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 work 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 10 engineers at our company, it should take them 10 minutes to figure out you aren't a product manager.

(instrumental music) Today my guest is Jeanne Grocer. Jeanne was chief product officer at Stripe, where she built their very early sales team from the ground up. She's currently COO at Vercel, where she oversees marketing, sales, customer success, revenue ops, and field engineering. Jeanne 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 Diett 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 of a ton of incredible products, including Devin, Lovable, Replit, Bolt, n8n, Linear, Superhuman, Descript, Whisperflow, Gamma, Perplexity, Warp, Granola, Magic Patterns, Raycast, Shape your HD, Mobinhand, Stripe, Atlas. Head on over to lennysnewsletter.com and click Product Pass. With that, I bring you Jeanne Grocer after a short word from our sponsors. This episode is brought to you by Datadog, now home to Eppo, 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. Once you know where to focus, experiments prove what works. I saw this firsthand when I was at Airbnb, where our experimentation platform was critical for analyzing what worked and where things went wrong, and the same team that built the experimentation at Airbnb built Eppo. Datadog then lets you go beyond the numbers with Session Replay. Watch exactly how users interact with heat maps and scroll maps to truly understand their behavior. And all of this is powered by feature flags that are tied to real-time data so that you can roll out safely, target precisely, and learn continuously. Datadog is more than engineering metrics. It's where great product teams learn faster, fix smarter, and ship with confidence. Request a demo at datadoghq.com/lenny. That's datadoghq.com/lenny. This episode is brought to you by Lovable. Not only are they the fastest-growing company in history, I use it regularly and I could not recommend it more highly. If you've ever had an idea for an app but didn't know where to start, Lovable is for you. Lovable lets you build working apps and websites by simply chatting with AI. Then you can customize it, add automations, and deploy it to live domain. It's perfect for marketers spinning up tools, product managers prototyping new ideas, and founders launching their next business. Unlike no-code tools, Lovable isn't about static pages. It builds full apps with real functionality, and it's fast. What used to take weeks, months, or years you can now do over a weekend. So if you've been sitting on an idea, now is the time to bring it to life. Get started for free at lovable.dev. That's lovable.dev. (instrumental music) Jeanne, thank you so much for being here and welcome to the podcast.