In January, when Airbnb started stocking its ranks with executives to lead its hotel expansion, it turned to former hotel executives. This week, Airbnb changed things up, shuffled the deck, and hired a former Booking EMEA executive, Andrea D'Amico, to lead its hotel push. Airbnb's biggest competitors have always been online travel agencies, not hotels, and Airbnb needed someone versed in the independent and boutique hotel space who knows how to build that business.
D'Amico happened to be CEO of WeRoad, a tour operator and experiences company, until this week. In addition to hiring away D'Amico, Airbnb led a $58 million Series C funding round for WeRoad, took a 10% stake, and got a seat on the board. D'Amico is also still on the board. A very cozy arrangement. Airbnb's Brian Chesky likes the partner first, acquire later approach, and that could turn out to be the WeRoad playbook as a way to grow Airbnb's experiences business if everything falls into place. So the whole thing looks like a two-fer — scale up hotels and experiences at the same time.
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EDITOR’S PICKS
Airbnb Names Booking.com Veteran in Hotel Leadership Shakeup
May 26, 2026
The hotel leadership shuffle represents somewhat of an about-face for Airbnb as it opts for a leader with online travel agency experience rather than a hotel brand track record. Still, these are early days for Airbnb hotels, and there is plenty of time to get things right.
Expedia To Acquire CarTrawler in Second B2B Deal of 2026
May 20, 2026
Expedia CEO Ariane Gorin, who ran its B2B unit before becoming CEO two years ago, is giving Parades the freedom and resources to expand the business. Expedia now faces the complexity of integrating two new businesses: Tiqets and CarTrawler.
SKIFT PODCAST NETWORK
While nearly every tech company is racing to put AI front and center, Airbnb is taking a different approach.
In this clip from The Skift Travel Podcast, Sarah Kopit and Seth Borko discuss Brian Chesky’s product philosophy and why Airbnb’s latest launch focused more on people than AI.
Instead of building the next chatbot, Airbnb is using AI behind the scenes to improve discovery, analyze reviews, and help travelers find the right stay for specific use cases.
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