The chairman of Expedia
After joining Expedia in 2006, Okerstrom quickly rose through the ranks and was considered a key player in the business before coming CEO. He was a close ally to original CEO Dara Khosrowshahi, who had founded Expedia and left the company a few years ago to become the CEO of embattled ride-share company Uber
Okerstrom talked about making a "frictionless" travel experience for the millions of customers that book through the travel site each year. The former CEO discussed in a recent conference how Expedia had so many different components to its travel business-flights, hotels, rental cars, travel insurance, and several other ventures as a part of its overall strategy-but not much in the way of connecting those ventures into a broader experience for the user. He wanted to make the customer experience on Expedia frictionless to better sell the overall scope of what the travel service had to offer. However, these changes did not do much to push the stock's price higher, and now Diller has to find new leadership as the travel industry changes.