Notion CEO Ivan Zhao Introduces Jazz Mode For AI-Era Companies

BHBrian Halligan@bhalligan

🚨NEW Long Strange Trip episode just dropped: Ivan Zhao, CEO of Notion @jack gave us the circular org chart. @brian_armstrong gave us player-coach. @ivanhzhao just added Jazz Mode. @NotionHQ is one of the clearest examples of a great SaaS company making the successful leap into becoming an AI company. That transition is much harder than it looks. @ivanhzhao is the definition of a Refounder, and has rebuilt his company nearly three times. Anyone who is looking to move into this new era, the “jazz era” should listen to this one 👇 Notes from our chat: 1. The Next Evolution to companies is structured freedom You need operators who can improvise and contribute creatively without waiting for orders. Think jazz band over marching band. Leaders must build teams that riff off each other dynamically rather than blindly following a rigid sheet of music. 2. Build a barbell engineering team Pair hyper senior architectural minds with junior talent. Senior leaders provide the taste and direction that language models lack, while junior engineers manage fleets of coding agents to execute the vision. 3. The best companies reinvent themselves When a startup stalls, incremental pivots rarely save it. Sometimes you must cleanly sever the past and start fresh. True technological shifts shouldn't feel like feature updates; they should feel existential. Interacting with frontier models should command a complete re-evaluation of your company's purpose. If a founder hasn't built with AI to feel this paradigm shift firsthand, they cannot find a new path forward. 4. Why Wartime is More Fun Peacetime in SaaS was comfortable, but wartime is where companies actually feel alive. When survival is on the line, the stakes are higher, and a shared, urgent purpose amplifies meaning for everyone. 5. Hire people who can blur traditional roles The best Notion hires have always blurred lines: designers who code, PMs who ship, engineers with taste. Baseline capability is no longer the bottleneck. The premium is now on a candidate's energy, optimism, and fundamental taste across multiple areas. 6. Acqui-hire founders aggressively As companies scale, they naturally calcify and slow down. The antidote is systematically acquiring early-stage startups just for the founders. Ex-founders act as aggressive machinery, breaking old patterns and forcing the organization to regenerate. 7. Financials March, Product Strategy Jazzes You cannot build a rigid product roadmap anymore because the underlying technology shifts too rapidly. Financial planning is the only system that still requires predictability; product strategy must be entirely fluid and improvisational. 8. Make compensation radically more meritocratic The SaaS era of "peanut buttering" compensation across the entire team is over. Companies must transition to extreme meritocracies to reward top performers. 9. Don’t reinvent the wheel unless you must Notion tried to first principle their way into sales. Eventually, they realized that was just plain wrong. Founders waste years trying to creatively invent a new sales system when the classic playbook works best. 10. Decentralizing the CMO Traditional marketing departments move too slowly to keep up with modern shipping cadences. The solution for Notion was to rip the CMO org apart and embed storytelling directly next to the product team. Demand generation now strictly serves the sales function. Lots lots more on this one. Ivan, as stylish as ever, was a blast. Enjoyed this one a lot. (links below) 👇👇 00:00 Introduction 02:22 From Founder Mode to AI Org 11:00 Hiring for Taste and Agency 24:28 Refounding Notion in Kyoto 30:27 Craft Versus Commerce 32:26 When to Refound 34:07 GPT-4 Refounding Shock 45:35 Leadership and Founder Energy 53:17 Sales Culture and Closing Thoughts