Ep. 30 The Best Time Ever to Be in Sales | Jeanne DeWitt Grosser, COO @ Vercel

<p>Vercel COO Jeanne DeWitt Grosser thinks this is the best time in history to be in sales — even as her own team automates away half of RevOps. Fresh off building go-to-market at Stripe through hypergrowth, she breaks down how to move up-market without blowing up your roadmap, why "maybes will kill you," and what AI actually changes about the job.</p><p>This episode is brought to you by Stifel Bank — trusted banking and venture debt partner for Sierra Ventures' portfolio. Learn more at <a href="www.stifel.com" target="_blank" rel="ugc noopener noreferrer">stifel.com</a>.</p><p>Chapters:<br />(0:00) "Maybes will kill you"<br />(1:24) Meet Jeanne DeWitt Grosser, COO of Vercel<br />(2:36) Google → Dialpad → Stripe → Vercel<br />(5:30) Building Stripe's sales machine from scratch<br />(9:53) Why moving up-market is a company decision<br />(16:08) AI-native companies &amp; the forward-deployed engineer debate<br />(27:12) Whales, buffaloes, and fins<br />(32:25) Treating GTM as a product<br />(44:00) Why it's the best time ever to be in sales<br />(50:47) Building GTM tools with "half a human"<br />(59:10) The AI-era salesperson: what changes, what doesn't</p><p><br /></p><p>Where to find Jeanne:</p><ul><li>LinkedIn: <a href="https://www.linkedin.com/in/jeannedewitt/" rel="ugc noopener noreferrer" target="_blank">https://www.linkedin.com/in/jeannedewitt/</a></li><li>Company: <a href="https://vercel.com" rel="ugc noopener noreferrer" target="_blank">https://vercel.com</a></li></ul>