Anthropic’s first technical PM on token maxing, the jagged edge, and living in the future | Dianne Penn

Dianne Penn, Anthropic's first technical product manager, joined in 2023 when the product team had five engineers and has since shipped every model from Claude 2 through Fable, and helped incubate Claude Code, MCP, Skills, computer use, tool use, and reasoning. In an interview, she discussed Anthropic's early days, the eval-driven development loop, and how Claude's willingness to push back is key to its success.

Dianne Penn is Head of Product for Anthropic’s AI Research and Labs teams. She joined in 2023 as Anthropic’s first technical product manager, when the entire product team was five engineers, and has since helped ship every model from Claude 2 through Fable, and helped incubate Claude Code, MCP, Skills, computer use, tool use, and reasoning. Before Anthropic, she helped build Alexa’s AI at Amazon and, before that, traded high-yield bonds at JP Morgan Chase. Listen on YouTube, Spotify, and Apple Podcasts In our in-depth conversation, we discuss: What Anthropic’s early days were like The inflection points that turned Anthropic from an underdog into the fastest-growing company in history How exactly Claude got so good at coding The eval-driven development loop her team is pioneering How to find joy in AI when everything is moving this fast Why Claude’s willingness to push back is key to its success Where human judgment remains irreplaceable Brought to you by: WorkOS —Make your app enterprise-ready, with SSO, SCIM, RBAC, and more Mercury —Radically different banking, now with Command Where to find Dianne Penn: • LinkedIn: linkedin.com/in/dianne-na-penn http://linkedin.com/in/dianne-na-penn Referenced: • Anthropic: https://www.anthropic.com https://www.anthropic.com • Golden Gate Claude: https://www.anthropic.com/news/golden-gate-claude https://www.anthropic.com/news/golden-gate-claude • Dario Amodei’s website: https://darioamodei.com https://darioamodei.com • Scaling Laws and Interpretability of Learning from Repeated Data: https://www.anthropic.com/research/scaling-laws-and-interpretability-of-learning-from-repeated-data https://www.anthropic.com/research/scaling-laws-and-interpretability-of-learning-from-repeated-data • Tokenmaxxing: How Top Builders Use AI To Do The Work Of 400 Engineers: https://www.ycombinator.com/library/Pa-tokenmaxxing-how-top-builders-use-ai-to-do-the-work-of-400-engineers https://www.ycombinator.com/library/Pa-tokenmaxxing-how-top-builders-use-ai-to-do-the-work-of-400-engineers • Garry Tan on X: https://x.com/garrytan https://x.com/garrytan • Anthropic co-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann • Anthropic’s CPO on what comes next | Mike Krieger co-founder of Instagram : https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next • Introducing Labs: https://www.anthropic.com/news/introducing-anthropic-labs https://www.anthropic.com/news/introducing-anthropic-labs • Louis CK | about airplane Wi Fi: https://www.youtube.com/watch?v=me4BZBsHwZs https://www.youtube.com/watch?v=me4BZBsHwZs • What happens after coding is solved? | Fiona Fung Manager of the Claude Code and Cowork Teams : https://www.lennysnewsletter.com/p/building-the-most-ai-pilled-engineering https://www.lennysnewsletter.com/p/building-the-most-ai-pilled-engineering • The Anthropic Hive Mind: https://steve-yegge.medium.com/the-anthropic-hive-mind-d01f768f3d7b https://steve-yegge.medium.com/the-anthropic-hive-mind-d01f768f3d7b • How to build a company that withstands any era | Eric Ries, Lean Startup author: https://www.lennysnewsletter.com/p/how-to-build-a-company-that-withstands https://www.lennysnewsletter.com/p/how-to-build-a-company-that-withstands • Fallout on Prime Video: https://www.amazon.com/dp/B0CN4GGGQ2 https://www.amazon.com/dp/B0CN4GGGQ2 • Fallout video game : https://fallout.bethesda.net https://fallout.bethesda.net • Claude Tag: https://www.anthropic.com/news/introducing-claude-tag https://www.anthropic.com/news/introducing-claude-tag Recommended books: • Crucial Conversations: Tools for Talking When Stakes Are High : https://www.amazon.com/dp/0071771328 https://www.amazon.com/dp/0071771328 • How to Raise an Adult: Break Free of the Overparenting Trap and Prepare Your Kid for Success : https://www.amazon.com/How-Raise-Adult-Overparenting-Prepare/dp/1627791779 https://www.amazon.com/How-Raise-Adult-Overparenting-Prepare/dp/1627791779 • Incorruptible: Why Good Companies Go Bad... and How Great Companies Stay Great : https://www.amazon.com/dp/B0FWZZBPZB https://www.amazon.com/dp/B0FWZZBPZB Production and marketing by https://penname.co/ https://penname.co/ . For inquiries about sponsoring the podcast, email email protected /cdn-cgi/l/email-protection 7d0d12191e1c0e093d11181313040f1c1e1514090e1604531e1210 . Lenny may be an investor in the companies discussed.