How to Reorg After AI Changes Everything | Block's Owen Jennings on the a16z Show

David Haber speaks with Owen Jennings, executive officer and business lead at Block, about how the company rebuilt itself around AI agents, small squads, and internal tools like Goose and Builder Bot after restructuring more than 40% of its workforce. They discuss what it took to execute a major restructuring, how teams of three are now doing what teams of 14 used to, and how Block is shipping AI-native products like Money Bot and Manager Bot that generate custom interfaces on the fly for tens of millions of users. Timestamps: 0:00—Introduction 6:06—How the RIF Actually Executed 9:08—The Most Meaningful Difference in How We're Operating 12:57—AI Infrastructure Build Across the Org 17:09—The Shape of the Business: Square, Cash App, Afterpay 20:00—From Static UI to Generative UI 23:23—Defensibility in the AI Era Read the full transcript here: https://www.a16z.news/s/podcast Resources: Follow Owen Jennings on X: https://twitter.com/owenbjennings Follow David Haber on X: https://twitter.com/dhaber Stay Updated: If you enjoyed this episode, be sure to like, subscribe, and share with your friends! Find a16z on X: https://twitter.com/a16z Find a16z on LinkedIn: https://www.linkedin.com/company/a16z Listen to the a16z Show on Spotify: https://open.spotify.com/show/5bC65RDvs3oxnLyqqvkUYX Listen to the a16z Show on Apple Podcasts: https://podcasts.apple.com/us/podcast/a16z-podcast/id842818711 Follow our host: https://x.com/eriktorenberg Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see http://a16z.com/disclosures.