Mike Cannon-Brookes is the Co-Founder and CEO of Atlassian, the company behind Jira, Confluence, Trello and Loom. Atlassian generated $6.5BN in ARR in 2026, and serves more than 350,000 customers, including over 85% of the Fortune 500. Today, Mike is leading its expansion into enterprise AI through Rovo and the Teamwork Graph, connecting company knowledge with AI agents. ----------------------------------------------- Timestamps: 00:00 Intro 01:24 Do AI Agents Turn Traditional Software Into Just Databases? 03:31 Why “Headless” Software Is a Brainless Bet 05:02 Why Design Becomes More Important in the AI Era 08:46 Is Company Context the Real Moat in Enterprise AI? 10:17 The Biggest Unsolved Design Problems With AI Agents 14:14 Will We Stop Caring Whether Content Is AI-Generated? 17:04 Will Enterprises Ever Trust Chinese AI Models? 21:21 Is Building Your Own AI Model a Losing Bet? 25:35 Can AI Startups Survive When They Finally Have to Care About Costs? 28:36 Why Model Routing Will Be...