AI’s third era: the rise of persistent AI coworkers | Tara Seshan (OpenAI’s product lead)

Tara Seshan leads product for ChatGPT Work at OpenAI (alongside previous podcast guest Andrew Ambrosino, who’s her engineering manager). Before OpenAI, Tara spent over six years at Stripe, where she joined as one of the first five product managers. She went on to lead product for Watershed, which Time magazine named one of the best inventions of 2022, and she is also a founder and Thiel Fellow. Most personally meaningful to me: Tara is one of the three inaugural Lenny’s Newsletter Fellows, a program I ran a couple of years ago to spotlight the most exciting up-and-coming product leaders. *In our in-depth conversation, we discuss:* 1. The shift from “rowing” to “steering,” and why human judgment and ambition will become differentiators as AI takes on execution 2. How OpenAI thinks about building for model capabilities two to three months out 3. OpenAI’s best internal memes, such as “Is this maximally accelerated?” and “Are you mainlining it yet?” 4. Why ambition is the new bottleneck for companies, and why elevating others’ ambitions is now the key part of the PM job 5. Writing as thinking vs. writing as reporting *Brought to you by:* WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lenny Mercury—Radically different banking, now with Command: https://mercury.com/ *Episode transcript:* https://www.lennysnewsletter.com/p/ais-third-era-the-rise-of-persistent *Archive of all Lenny's Podcast transcripts:* https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 *Where to find Tara Seshan:* • X: https://x.com/tarstarr • LinkedIn: https://www.linkedin.com/in/tarstarr • Newsletter: https://substack.com/@taraseshan *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 (02:18) What makes OpenAI’s culture so different (06:42) Why AI product strategy is all about fast experimentation (09:02) How the PM role is changing (10:50) The shift from rowing to steering (15:35) What changes when agents become coworkers (20:05) Why ambition matters more than ever (26:39) Building products for models that do not exist yet (29:21) How ChatGPT’s Chat and Work modes differ (34:01) How OpenAI ships so quickly at scale (39:14) The vibe shift happening…