WorkOS

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

Aug 30, 2026 · 1:21:45

Tara Seshan, OpenAI's product lead for Codex and ChatGPT Work, tells Lenny Rachitsky that AI is entering a third era of persistent AI coworkers, where human judgment and ambition—not execution—become the differentiator. She explains why OpenAI builds for model capabilities two to three months out, citing memes like 'Is this maximally accelerated?' and 'Are you mainlining it yet?' as the product-development test. She says the PM job now centers on sharp hypothesis testing and elevating others' ambitions, and describes ChatGPT's Chat, Work, and Codex modes converging on a single box that picks the right harness. She also distinguishes writing as thinking (never automate) from writing as reporting (automate), and shares Sutter Hill's lesson that product marketing fit can precede building.

84 minutes of enterprise sales alpha | Jen Abel

Aug 23, 2026 · 1:24:57

Jen Abel — co-founder of JJellyfish and GM of enterprise sales at State Affairs — joins Lenny Rachitsky to map the enterprise sales cycle, arguing it takes closer to 15 steps than the standard five-stage CRM funnel, via a hypothetical $100K deal with SpaceX's legal team. She explains the pincer model for reaching the executive and N-minus-one at once, and treats the intro call as the moment to extract maximum intelligence before any demo. She details pre-demo prep calls, demoing only the 20% of the product that matters, a two-to-three-day pilot with jointly defined success, and pricing talks that avoid discounting. The episode finishes with papering redlines, procurement timelines, signature—and enterprise win rates of 30–35%, adding that if your win rate is higher, your price is too low.