Where Airbnb's CEO sees the company headed
⚠️ All rights reserved. Cite this piece as 'ONDA (온다)' when quoting.
On May 1st, Airbnb held a media event in Los Angeles to unveil its "Icons" category — 11 wildly unique stays you can win through lottery draws.
That same day, travel industry outlet Skift published an interview with Airbnb CEO Brian Chesky. It's packed with hints about where Airbnb is headed.
Loyalty: Paid Membership YES, Points NO
In the Skift interview, Chesky said flat-out: "We will never create a points program. I hate that stuff." The best way to bring people back, he argued, is to make sure the place they stayed was excellent.
He did acknowledge why hotels run loyalty programs — it's about capturing account data.
Eventually, Airbnb will launch something loyalty-adjacent. But it won't look like points. Chesky pointed to Amazon Prime as his model. (Think Korea's "Coupang Wow" — a paid membership with perks like free shipping, free returns, exclusive deals, and streaming video.)
We don't know when Airbnb's paid tier will launch. But it's safe to say it won't just be discounts. Like Amazon Prime solves e-commerce friction (shipping fees, complex returns), Airbnb's program will likely tackle pain points unique to travel.
"Guest Favorites" Listings Backed by 500 Million Reviews
This was my favorite part of the interview. The interviewer told Chesky bluntly: "I never use Airbnb for work trips." The reason? Reliability.
Chesky shot back: Guest Favorites listings on Airbnb are more reliable than certain hotel brands (check out the full interview if you're curious which chain ^^;;).
He conceded that Airbnb doesn't offer everything hotels do. But he argued that Guest Favorites are still more dependable than midscale hotels.
What do you think?
AI Concierge in the Works
In this summer's update, Airbnb rolled out "reactions" (emoji responses to guest messages) and AI-powered quick-reply suggestions for hosts fielding common questions. AI is top of mind for every tech company right now.
Chesky revealed that the co-founder of Apple's Siri has joined Airbnb, and that he's more optimistic about AI than ever.
He believes apps will evolve into personalized concierge services — learning about users over time. That's why Airbnb's first big generative AI push will be in customer service.
But he's realistic: no one has shipped truly transformative generative AI experiences yet. So Airbnb still needs more time.
Meanwhile, Airbnb's new "Icons" category launched this summer — 11 unforgettable stays bookable at extremely low prices (sometimes free). You can browse them in the Airbnb app now. These two were my favorites:
Stay in the Floating Up House — The actual house from Pixar's Up, suspended in the sky by over 8,000 balloons. Every detail of Carl's home is faithfully recreated, set against the red rock canyons of Abiquiú, New Mexico.
Step Inside X-Men '97 — Ever wanted to be an X-Man? This is a 2D recreation of the X-Mansion from the Marvel animated series, located in Westchester, New York. Discover your superpower and train in the Danger Room.