On June 1, 2026, Expedia Group appointed former Pinterest executive Bill Watkins as Senior Vice President and General Manager. While the travel giant shifts its leadership team, its former chief executive is busy looking back at the company's foundational business model.
Speaking on Invest Like the Best with Patrick O'Shaughnessy, current Uber chief Dara Khosrowshahi looked back at his time running Expedia alongside media mogul Barry Diller. Khosrowshahi recalled, "I've been at Expedia for thirteen years, CEO working with Barry Diller, and loved the experience," but contrasted his past role with his current one. He explained that Expedia was historically a "demand first company" where "we were really focused on demand, how many consumers can we get to the website," whereas Uber operates as a supply-led marketplace.
This structural difference hasn't stopped Uber from tapping into Expedia's deep well of inventory. Dara Khosrowshahi detailed a partnership where Expedia provides hotel supply directly to Uber's travel ecosystem, capitalizing on users who "travel a lot" and open the app immediately upon landing.
As Bill Watkins steps into his new role at Expedia, he will have to navigate this duality. The company must continue to capture consumer demand on its own platforms while increasingly acting as the backend engine for other tech giants.