Channel
Interviewed Person
Jeanne Grosser
Jeanne DeWitt Grosser built world-class GTM teams at Stripe, Google, and, most recently, Vercel, where she serves as COO and oversees marketing, sales, customer success, revenue operations, and field engineering. She transformed Stripe’s early sales organization from the ground up and advises founders on GTM strategy. *We discuss:* 1. Why GTM is becoming more strategically important in the AI era 2. The rise of the GTM engineer 3. A primer on segmentation 4. How to build a sales org that engineers and product teams respect 5. The changing calculus of build vs. buy for go-to-market tools in the AI era 6. Why most customers buy to avoid pain rather than to gain upside *Brought to you by:* Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lenny Lovable—Build apps by simply chatting with AI: https://lovable.dev/ Stripe—Helping companies of all sizes grow revenue: https://stripe.com/ *Transcript:* https://www.lennysnewsletter.com/p/what-the-best-gtm-teams-do-differently *My biggest takeaways (for paid newsletter subscribers):* https://www.lennysnewsletter.com/i/179503137/my-biggest-takeaways-from-this-conversation *Where to find Jeanne DeWitt Grosser:* • X: https://x.com/jdewitt29 • LinkedIn: https://www.linkedin.com/in/jeannedewitt *Where to find Lenny:* • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ *In this episode, we cover:* (00:00) Introduction to Jeanne DeWitt Grosser (05:26) Defining go-to-market (08:43) The evolution of go-to-market roles (11:23) The rise of the go-to-market engineer (14:21) Implementing AI in sales processes (15:28) Optimizing sales with AI agents (23:47) Defining sales roles: SDRs and AEs (26:04) When to hire a GTM engineer (29:04) Hiring and scaling sales teams (30:50) The ideal go-to-market engineer (34:24) The go-to-market tool stack (40:39) Advice on building a great sales bot (44:34) Vercel’s unfair advantage (46:37) Go-to-market as a product (47:04) Innovative sales tactics at Stripe (52:38) Effective go-to-market tactics (01:00:37) Segmentation strategies (01:09:31) Building a sales org that engineers love (01:14:00) Thoughts on PLG and pricing (01:16:44) Sales compensation and hiring (01:19:24) Lightning round and final thoughts *Referenced:* • Vercel: https://vercel.com • Stripe: https://stripe.com • Rosalind Franklin: https://en.wikipedia.org/wiki/Rosalind_Franklin • Ben Salzman on LinkedIn: https://www.linkedin.com/in/bensalzman • SDK: https://ai-sdk.dev/docs/introduction • Gong: https://www.gong.io • Lyft: https://www.lyft.com • Instacart: https://www.instacart.com • DoorDash: https://www.instacart.com • “Sell the alpha, not the feature”: The enterprise sales playbook for $1M to $10M ARR | Jen Abel: https://www.lennysnewsletter.com/p/the-enterprise-sales-playbook-1m-to-10m-arr • A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch): https://www.lennysnewsletter.com/p/a-step-by-step-guide-to-crafting • Kate Jensen on LinkedIn: https://www.linkedin.com/in/kateearle • Lessons from scaling Stripe | Claire Hughes Johnson (former COO of Stripe): https://www.lennysnewsletter.com/p/lessons-from-scaling-stripe-tactics • Atlassian: atlassian.com _Production and marketing by https://penname.co/._ _For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com._ Lenny may be an investor in the companies discussed.
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 Jenna Ael 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 merger. 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 or that doesn't feel like a sales or 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 Gan Grosser. Gan was chief product officer at Stripe where she built their very early sales team from the ground up. She's currently COO at Versell where she oversees marketing, sales, customer success, revenue ops, and field engineering. Gene 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 goto 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 goto 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 Deiet 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 Devon, Lovable, Repid, Bolt, NAD, Linear, Superhum, Dcript, Whisper Flow, Gamma, Perplexity, Warp, Granola, Magic
Patterns, Raycast, Shapeyard D, Mob, and Hand, Stripe Atlas. Head on over to lennisnewsletter.com and click product pass. With that, I bring you Jean 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. 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 experimentation at Airbnb built EPO. Beta do then lets you go beyond the numbers with session replay.
