Ian Silber is the head of product design at OpenAI, where he has led the design of ChatGPT, Codex, and all of OpenAI’s product experience for the past three years. Before OpenAI, he was at Artifact, the AI-powered news app built by the founders of Instagram. Prior to that, he spent eight years at Instagram, where he worked on products including Reels. Ian is one of the most consequential designers working in AI today, and he takes us inside how OpenAI designs ChatGPT, Codex, and the future of how we will interact with AI.
Why Ian believes this is the best time in history to be a product designer
Why engineers 10x’d with AI but design teams haven’t
What OpenAI looks for when hiring designers
“Just do less”: Ian’s counterintuitive advice to his designers
The future of ChatGPT as a super app
Where humans still win: user understanding, invention, and point of view
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• LinkedIn: https://www.linkedin.com/in/iansilber
• Website: https://iansilber.com
• OpenAI: https://openai.com
• How tech workers are feeling in 2026: a workforce splitting in two: https://www.lennysnewsletter.com/p/how-tech-workers-are-feeling-in-2026
• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom
• 3 Spiderman Pointing meme template: https://www.kapwing.com/explore/3-spiderman-pointing-meme-template
• OpenAI Codex lead on the new shape of product work | Andrew Ambrosino: https://www.lennysnewsletter.com/p/openai-codex-lead-on-the-new-shape
• Notion: https://www.notion.com
• The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude): https://www.lennysnewsletter.com/p/the-design-process-is-dead
• Joel Lewenstein on LinkedIn: https://www.linkedin.com/in/joel-lewenstein
• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next
• ChatGPT Work: https://openai.com/chatgpt-work
• 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
• Please Stop the AI Confidence Theater: https://www.elenaverna.com/p/please-stop-the-ai-confidence-theater
• The new AI growth playbook for 2026: How Lovable hit $200M ARR in one year | Elena Verna (Head of Growth): https://www.lennysnewsletter.com/p/the-new-ai-growth-playbook-for-2026-elena-verna
• Maybe Happy Ending: https://www.maybehappyending.com
• The Invite: https://www.imdb.com/title/tt14173636
• Rivian: https://rivian.com
• Waymo: https://waymo.com
• Groupon: https://www.groupon.com
• How a VC and a tech founder used AI to launch a brick-and-mortar business in their spare time | Andrew Mason (CEO of Descript) and Nabeel Hyatt (General Partner at Spark Capital): https://www.lennysnewsletter.com/p/how-a-vc-and-a-tech-founder-used
• Andrew Mason on X: https://x.com/andrewmason
• Kevin Systrom on LinkedIn: https://www.linkedin.com/in/kevinsystrom
• Sam Altman on X: https://x.com/sama
• The Design of Everyday Things: https://www.amazon.com/dp/0465050654
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Lenny may be an investor in the companies discussed.