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AI’s third era: the rise of persistent AI coworkers | Tara Seshan (Product Lead ChatGPT Work)

Lenny's Podcast

Hosted by Lenny Rachitsky

1h 21m
Transcript

Original podcast

Summary

Written by a model from the transcript; not yet reviewed.

This episode of Lenny's Podcast features Tara Seshan, Product Lead for Codex and ChatGPT Work at OpenAI. Seshan discusses the evolution of AI products from simple chat interfaces to agents and persistent coworkers, explaining how OpenAI operates more like a collection of internal founders rather than a top-down hierarchy. She and the host discuss the shift from theoretical, academic product planning to rapid, empirical testing, noting that a PM's core job is defining the single most important hypothesis and running fast test loops. Seshan also shares practical tips on utilizing AI to build personal software and sites, the importance of human writing as a tool for deep thinking, and how the team builds for future model capabilities two to three months out.

  • Prioritize rapid empirical testing and defining a core product hypothesis over writing long, theoretical strategy documents. 0:44
  • Write your product briefs and strategic plans yourself rather than outsourcing thinking to AI models. 53:36
  • Focus your product development on where model capabilities will be in two to three months rather than where they are today. 27:27
  • Test product narratives and positioning early, as excellent product marketing fit can precede building the actual product experience. 1:03:28

Chapters

  1. 0:00
    Defining AI’s Third Era

    The hosts introduce the concept of a persistent AI coworker as the next evolution of AI products.

  2. 0:30
    Product Management in Rapid AI

    Discussion of how product managers must adapt to fast-moving AI capabilities and prioritize empirical testing.

  3. 1:18
    Tara Seshan’s Background

    Introduction of Tara Seshan, her career path, and her role leading ChatGPT Work at OpenAI.

  4. 3:12
    OpenAI’s Founder‑Led Culture

    Exploration of OpenAI’s founder‑led, low‑top‑down structure and its impact on product ownership.

  5. 8:20
    Ambition and Product Growth

    Discussion of how AI tools expand ambition, enabling rapid, ambitious product experiments.

  6. 16:26
    The Persistent Coworker Vision

    Tara explains the goal of making agents act like teammates, collaborating across teams.

  7. 19:14
    Agent‑Powered Workflows

    Details on how agents can handle higher‑level tasks and the importance of data access and infrastructure.

  8. 29:40
    ChatGPT Work Mode Explained

    Breakdown of ChatGPT’s modes—Chat, Codex, and Work—and how they serve different user needs.

  9. 34:03
    Balancing Scale and Innovation

    Challenges of integrating new AI products with the massive user base of ChatGPT.

  10. 37:55
    Iterative Product Culture

    OpenAI’s focus on rapid iteration, user feedback, and shipping over perfection.

  11. 46:18
    Human Value in an AI‑Driven World

    Reflection on the enduring importance of human accountability and creativity alongside AI.

  12. 47:05
    Introduction and Human Authorship

    The host discusses the enduring value of human creativity and collaboration in software development, contrasting it with AI’s capabilities.

Highlights

  • 0:24

    Building for Future Model Capabilitiesinsight

    Building for where models are today or where they will be in a year are both equally wrong, leaving a strict two-to-three-month window for effective product development.

  • 3:22

    OpenAI Operates as Founders-Ledinsight

    OpenAI operates with minimal top-down direction where product leaders act akin to founders with a very short distance to the market.

  • 7:48

    The Shift from Academic to Empiricalstrategy

    The rapid pace of AI requires moving away from long academic reasoning docs toward fast user testing and empirical validation.

  • 11:22

    Future Work Looks Like Steeringinsight

    The future of knowledge work will transition from manual rowing to steering agents that handle the heavy lifting at higher levels of abstraction.

  • 20:41

    Elevating Ambitions with AI Toolsstrategy

    AI tools allow individuals to expand their execution range, requiring product managers to elevate team ambitions rather than just automate rote tasks.

  • 36:48

    Done Is Better Than Perfectstrategy

    In fast-moving AI markets, shipping a transformative product early and iterating on user feedback is more valuable than endless pre-launch polish.

  • 53:20

    Writing as Thinking vs Reportinginsight

    While AI can be used to automate reporting, writing-as-thinking must remain a human-driven discipline to prevent cognitive atrophy.

Quotes

  • “You fail if you build for where the models are now. You fail if you build for where you think the models will be in a year. Both outcomes are equally wrong.”
    Unnamed speaker · 27:27
  • “Being prolific and empirical is way more important than being academic or theoretical.”
    Unnamed speaker · 0:38
  • “Elevating others ambitions or reminding them of what's possible here is a huge part of the product management role.”
    Unnamed speaker · 24:30
  • “The level of like top‑down direction at OpenAI is extremely limited relative to places I've worked for prior.”
    Unnamed speaker · 3:34
  • “The part to me that actually felt the most surprising is that many companies I've worked for, in fact, all the companies I've worked for in the past have been founder‑led.”
    Unnamed speaker · 3:12
  • “The only way to build is two to three months.”
    Unnamed speaker · 27:47
  • “I also think the human brain continues to be valuable in, like, how we care for each other and relate to one another.”
    Unnamed speaker · 47:34
  • “One of the most exciting ways that I use AI in work is actually build sites all the time now.”
    Unnamed speaker · 48:55
  • “I literally with a prompt say like, build me this exact tool that I need to get this thing done and it just does it.”
    Unnamed speaker · 50:03
  • “I previously had a manager who told me that the right thing to always do is write a doc to 70% completion.”
    Unnamed speaker · 57:29
  • WorkOS 5:33–6:43
  • Mercury 37:55–38:57
  • ChatGPT 1:19:18–1:20:06

About this episode

Tara Seshan leads product for Codex and 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 https://workos.com/lenny—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more Mercury https://mercury.com/command?utm_source=lennys&utm_medium=sponsored_newsletter&utm_campaign=26q3_brand_campaign—Radically different banking, now with Command — 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 inside Codex (42:20) Why traditional roles are beginning to blur (45:59) Where humans will continue to provide unique value (48:20) How Tara uses AI in her own work (51:38) The magic of the /visualize command (52:39) Writing to think versus writing to report (57:10) How to use AI without losing your ability to think (01:00:15) Tara’s biggest lesson from Sutter Hill (01:04:16) ChatGPT’s site output (01:05:01) Why knowledge work is becoming more like coding (01:07:55) Lightning round and final thoughts — Referenced: • Codex: https://chatgpt.com/codex • ChatGPT Work: https://openai.com/chatgpt-work • Stripe: https://stripe.com • Watershed: https://watershed.com • Thiel Fellowship: https://thielfellowship.org • Meet your Lenny’s Newsletter Fellows: https://www.lennysnewsletter.com/p/meet-your-lennys-newsletter-fellows • The rituals of great teams | Shishir Mehrotra of Coda, YouTube, Microsoft: https://www.lennysnewsletter.com/p/the-rituals-of-great-teams-shishir • The nature of product | Marty Cagan, Silicon Valley Product Group: https://www.lennysnewsletter.com/p/the-nature-of-product-marty-cagan • Product management theater | Marty Cagan (Silicon Valley Product Group): https://www.lennysnewsletter.com/p/product-management-theater-marty • Patrick Collison’s examples of fast projects: https://patrickcollison.com/fast • Inside ChatGPT: The fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley • Andrew Ambrosino on X: https://x.com/ajambrosino • Tyler Cowen’s website: https://tylercowen.com • OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai • “Chop wood, carry water” quote: https://buddhism.stackexchange.com/questions/15921/what-is-the-meaning-of-the-zen-quote-before-enlightenment-chop-wood-carry-wat • 4 questions Shreyas Doshi wishes he’d asked himself sooner | Former PM leader at Stripe, Twitter, Google: https://www.lennysnewsletter.com/p/shreyas-doshi-live • Alan Kay: https://en.wikipedia.org/wiki/Alan_Kay • Brie Wolfson on X: https://x.com/zebriez • The playbook for building high-talent-density teams | Adam Ward, Head of Talent at Cursor: https://www.lennysnewsletter.com/p/the-playbook-for-building-high-talent • Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein • Sutter Hill Ventures: https://shv.com • Snowflake: https://www.snowflake.com • Mike Speiser on LinkedIn: https://www.linkedin.com/in/mikespeiser • Footnotes and Tangents: https://footnotesandtangents.substack.com • The Power Broker Book Club: https://www.robertcaro.org/copy-of-six-books-six-ny-times-book • The Odyssey: https://www.imdb.com/title/tt33764258 • Rashomon: https://www.imdb.com/title/tt0042876 • Akira Kurosawa: https://en.wikipedia.org/wiki/Akira_Kurosawa • Kevin Kwok on LinkedIn: https://www.linkedin.com/in/kevinakwok • The Work You Do, the Person You Are: https://www.newyorker.com/magazine/2017/06/05/toni-morrison-the-work-you-do-the-person-you-are • Ari Weinstein on X: https://x.com/AriX • Sky: https://sky.app • Dylan Field live at Config: Intuition, simplicity, and the future of design: https://www.lennysnewsletter.com/p/dylan-field-live-at-config — Recommended books: • Barbarian Days: A Surfing Life: https://www.amazon.com/dp/0143109391 • Anna Karenina: https://www.amazon.com/Anna-Karenina-LEO-TOLSTOY/dp/8175993421 • The Power Broker: https://www.amazon.com/dp/0394720245 • War and Peace: https://www.amazon.com/War-Peace-Leo-Tolstoy/dp/8175992832 • Wolf Hall: https://www.amazon.com/dp/0312429983 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected] mailto:[email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com https://www.lennysnewsletter.com?utm_medium=podcast&utm_campaign=show-notes-no-free-preview-language

Transcript

0:00
1:21:44

15,839 words · 2 speakers

Speaker names marked are inferred from speaking time and the show’s known hosts — they are not voice-verified.

Topics

  • Work
  • Codex
  • OpenAI
  • Sites
  • Stripe
  • Anna Karenina
  • The Power Broker
  • The Odyssey
  • Notion
  • Thiel Fellowship

Page updated · transcript and summary are machine-generated