Can Uber’s New CEO Dara Khosrowshahi Turn It Around Like He Did Expedia?

Will Dara Khosrowshahi, the longtime CEO of Expedia Inc., be the right person at an opportune moment to help get Uber back on track as its new boss?

Many people will argue that Uber probably should have selected a qualified woman — and there are many — to head the company given the sexual harassment issues that came to light recently under now-ousted CEO Travis Kalanick. It didn’t, though. It did choose someone who has proven he could help weather a dot-com crash, 9/11, the 2008 economic collapse, and multiple rivals.

Plus, as an immigrant himself, Khosrowshahi has proven multiple times to be a progressive enough individual when it comes to opposing President Trump’s anti-immigrant and anti-travel policies, and the Expedia CEO has done much to encourage the advancement of women within Expedia. But we just don’t know if he has the skills to overturn Uber’s toxic internal culture. It’s not a one-person job, though, at any rate.

As Uber faces myriad other crisis points, including persistent financial losses,  regulatory issues, low morale within its ranks, and frustration among its fairly low-paid driver contractors, Khosrowshahi has ample experience in leading a multiyear effort to turn a company around.

He did it at Expedia.

Let’s go back to 2010. Expedia was getting embarrassed quarter after quarter with rival Booking.com consistently out-executing Expedia. It should be noted that Booking.com is still is miles ahead of Expedia in terms of growth and scale, but Expedia, until 2016, at least, had managed to narrow the gap

Let’s look at the numbers from 2010 to 2014, comparing Expedia and the Priceline Group’s gross bookings.

Expedia Inc. Gross Bookings and Room Night Growth, 2010-2014

Priceline Group Gross Bookings and Room Night Growth, 2010-2014

Source: Financial reports

Expedia is still a much smaller company than the Priceline Group and has had its own growth problems over the last year as it has been bogged down with integrating acquisitions, including Obitz Worldwide and HomeAway.

In the 2010 to 2014 period, though, Khosrowshahi and his Expedia team transitioned its myriad brands onto a common global technology platform, one that has enabled the business units to share inventory, as well as test and learn at a much more rapid clip.

Then in the 2014 to 2015 period, Expedia went on an acquisition tear, acquiring Wotif in Australia, and then-rivals Travelocity, Orbitz, and HomeAway, among other acquisitions.

In March 2015, I mentioned to Khosrowshahi that I had been expecting him to be fired during that rough patch of the prior four years.

Khosrowshahi conceded there were “tough days” and described how he and his team “walked through the fire together.”

“Listen, any time you’re the CEO of a public company, especially in a field as competitive as the travel field, your job is on the line every day,” Khosrowshahi said. “My job is on the line now.”

Khosrowshahi will certainly have his work cut out for him at the Uber CEO post given the company’s wide-ranging challenges, including a board of directors who seem to be at each others’ throats.

But his experience as a public company executive who has been tested under fire over the last two decades may be a valuable “get” for Uber. At least the Uber board apparently thinks so.

For Expedia, though, Khosrowshahi’s potential departure would come at an awkward time. The company is in the midst of its latest transition: Integrating HomeAway and becoming a force in alternative lodging as the world of accommodations is being revolutionized by Airbnb and others.

An abrupt departure from Expedia — with no apparent transition plan — might put that transition in peril.