Airbnb CEO Brian Chesky wants to let you in on a secret: many CEOs don’t know what’s happening inside their company.
That could explain why many big-time CEOs, including Chesky, have gone all-in on AI.
Speaking at the Skift Global Forum on Wednesday, Chesky said he’s built an AI system that helps him run the company and reduce meeting time.
“Most of us CEOs of big companies don’t really know what the hell’s going on in our companies, and so we have these things called meetings, which are just for us to figure out what’s going on, and well-intentioned people underneath us kind of manage us,” Chesky said during a virtual appearance at the conference.
When asked whether he’s personally shipping — releasing a finished product or update — Chesky said yes, but not for customers. “My whole job was, ‘how can I not need meetings to know what’s going on inside the company?'” he said.
The Airbnb cofounder said he’s used AI to develop a “brain” or “intelligence corpus” trained on 18,000 Keynote slides, 50,000 Google documents, and a ton of other company information. He also said he’s built a bunch of dashboards that help him understand what’s going on inside his own company.
“This intelligence layer means I now have total information,” he said, adding, “I’ve cut my meetings in half.”
Chesky’s full-fledged embrace of AI aligns with his stated goal for Airbnb: to become an AI-native company. He said Wednesday at the Skift forum that the company is “pretty much” there and that everyone on the executive team has been “AI-pilled.” Chesky said he personally set a goal to be as native with AI as he would be if he had grown up with the technology.
“I never wanted to be this person that it passed me by,” he said.
He’s not the only CEO embracing AI. A survey conducted by KPMG of 100 CEOs at large US companies earlier this year found that 77% said generative AI may have been overhyped, but its “disruptive potential” over the next five to 10 years is likely underhyped. Nearly 80% said they were allocating at least 5% of their 2026 capital budgets to AI.
AI has already transformed Airbnb. Chesky said Wednesday that the tech has allowed Airbnb to ship over 600 features this year, almost twice as many as last year, and that nearly half of its customer service requests are now handled by AI.
He also said Airbnb would be launching an AI agent next year — he’s previously said agents that can book trips for you were coming — and that it will have a new interface that is “much richer than a chatbot.”
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