Expedia: Dara Khosrowshahi (CEO)
The 12-year CEO, Dara Khosrowshahi, departed from the online travel agency and arrived as Uber CEO for a hefty ticket price that could top $200 million. Dara grew Expedia into one of the world’s most successful travel one-stops. During his tenure, Expedia’s share prices soared 8x while its market capitalization expanded by $18 billion. Looking to find the best deals, Khosrowshahi led the company an acquisition spree, buying Travelocity, Orbitz, Wotif, and others. In order to stay competitive against the likes of Kayak and Airbnb, Dara led the acquisition of HomeAway, which operates a string of vacation rental sites your DAD uses. Khosrowshahi was dubbed a comeback kid in 2015 after he led a multiyear transition placing Expedia on a global technology platform, and increasing hotel room growth after 3 years of stagnation. While there was a concern if he would remain at the helm prior to this turnaround, the company shifted gears and is now concerned with his departure, which comes at a crucial time after spending much of 2016 integrating its acquisitions. Khosrowshahi showed he had the chops to propel success in a consolidating travel industry. Expedia will need significant creative lift to keep from crashing.