Airbnb CEO Brian Chesky on why he’s deep in the product details

“We completely overhauled how we develop product development at Airbnb,” Chesky says.

Alex Kantrowitz
2 min readSep 30, 2023

Hi Everyone, I just sat down with Airbnb CEO Brian Chesky and published the interview on the Big Technology Podcast feed.

We talked about so much, including cleaning fees, building product, the difference between Amazon and Apple culture, and Airbnb’s restrictions in New York.

You can listen on Apple Podcasts, Spotify, or your podcast app of choice.

I found this conversation remarkable, not only because Chesky broke some news about Airbnb feature updates almost as soon as he sat down. But the deeper conversation examines the role of a leader inside a successful company, and how engaged they should be with customers and day-to-day decisions.

Listen, and you’ll hear Chesky talk about how Airbnb reimagined its product management role (it’s now product marketing) and how Chesky decided to go way deeper into the details than your typical big company CEO. Airbnb still has plenty of work ahead, but it was illuminating to hear how it will go about it.

“I actually stay in the details,” Chesky told me. “CEOs at S&P 500, Fortune 100 companies, I think most of them aren’t really in the details of their product. At some point, these companies get so big, that it’s pretty typical that you get a little detached, that it’s someone else’s job to listen to customers. But it’s not your job. And I’ve always wanted to be the kind of company that felt more like a startup.”

Then, he admitted where the company went wrong:

“As we went on this hyper growth rocket ship from 2009 to 2019, over the 10 year period, I think we got further and further removed from the customer. We went from us talking to customers, to hiring people to talk to customers, to people who manage people who manage people who talk to customers.”

Today, Chesky sits at the center of the company’s product decisions. He’s not dictating everything that’s built, but almost everything the company ships now comes through him. He shares much more in the podcast.

It’s rare to sit down with a CEO this amped about the product, how it’s built, how a company functions, and its role in the world. I hope you enjoy.

Again, you can listen on Apple Podcasts, Spotify, or your podcast app of choice.

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Alex Kantrowitz

Veteran journalist covering Big Tech and society. Subscribe to my newsletter here: https://bigtechnology.substack.com.