The proposed new CEO of Uber has spent a decade mastering one part of the travel economy. But Uber is a new and very different beast.
The selection of 48-year-old Dara Khosrowshahi to oversee the $70 billion company is going to be an enormous challenge for an executive who has no direct background in transportation.
Since 2005, Khosrowshahi has led the travel-booking site Expedia to become “one of the largest online travel companies in the world,” according to the company. Expedia has ridden the explosion in online bookings that have displaced traditional travel agents working out of brick-and-mortar offices across the U.S.
But Expedia has also had to confront a new class of upstart companies like Airbnb that offer new travel services, and to distinguish itself from other similar travel bookers, like Kayak. Under Khosrowshahi, Expedia aimed to keep pace with the new services, purchasing startup HomeAway for $3.9 billion in 2015, for instance.
He was well liked at Expedia: 94% of employees told the review site Glassdoor that they currently approved of his leadership.
“Dara is the smartest, most passionate and thoughtful executive I’ve worked with in 25 years,” said Burke Norton, former Salesforce and Expedia senior exec. “He has super high integrity and is a phenomenal leader — the kind of leader whom people would follow into a burning building."
Well, that conflagration would describe Uber, for sure! Analysts said they viewed him as a strong candidate for the position, noting he bluntly and presciently warned of a “dog’s breakfast” in the market before the financial crisis.
And Khosrowshahi’s experience running a complex, global company with a two-sided marketplace may prove useful when he accepts as expected the CEO role at Uber. Like at Expedia, his task is to turn unsold space — whether it’s an empty hotel room or an extra car seat — into revenue.
Born to a Muslim family in Iran, Khosrowshahi graduated from Brown University in 1991 and was originally trained as an engineer. He then spent seven years at the investment bank Allen & Company, followed by a few years at IAC, originally the parent company of Expedia, where he was mentored by media executive Barry Diller.
“Early on, I didn’t know what I was getting into,” Khosrowshahi said in an Expedia company video in 2013. “And I think for the first year, when I was running the company, I wasn’t a particularly good CEO.”
Khosrowshahi has some experience leading employees during a CEO transition — but never a workforce as divided as Uber’s, many of whom were loyal to ousted CEO Travis Kalanick.
But Khosrowshahi has one advantage if he takes the job, according to people within the company: He was not the hand-picked choice of Benchmark, the venture capital firm that sued Kalanick and whose nominee would as a consequence have been distrusted by employees.
The Expedia CEO does share at least one connection with Benchmark, though: Rich Barton, Expedia’s founder, is a Benchmark partner.
Khosrowshahi is leaving behind a hefty salary at Expedia, although he is likely to command top dollar at Uber, as well: In 2016, Khosrowshahi made $2.45 million, according to FactSet. The year prior, he made a bumper salary of $94.6 million for entering into a long-term employment agreement with Expedia — the agreement had his term expiring in 2020. That made him the highest paid U.S. CEO in 2015, according to Equilar.
He comes from a tech family: He is a cousin of investors Hadi and Ali Partovi, who grew up with Khosrowshahi in Iran and also went to high school with him in the U.S. Other family members work at Intel, Google Ventures and Allen & Company, according to the Partovis.
Hadi Partovi said Khosrowshahi was a popular student in high school, serving as class president, as well as captain of the soccer and lacrosse teams, adding that he also won the award for best all-around student. “We were cool wannabes, computer nerds, but he was really cool,” he joked.
Ali Partovi noted that his cousin has the skills necessary to deal with the turbulent waters at Uber. “Dara is such a statesman and has been that for decades,” he said. “In every scenario, when he speaks up, people listen to him.”
But Khosrowshahi does not appear to have spent extensive time in Silicon Valley, although he is well known in tech, nor does he have much of an obvious connection to Uber. His top rivals for the job, Hewlett Packard Enterprise CEO Meg Whitman and former General Electric CEO Jeff Immelt, similarly did not have any significant transportation experience.
He has, however, shown some affinity for on-demand transportation: Khosrowshahi, according to PitchBook, is a personal investor in Convoy, a company that has been described as “Uber for trucking,” and that could be an attractive acquisition for the ride-hailing giant down the line. For now, Convoy is a direct competitor to Uber’s similar service, UberFreight.
Khosrowshahi also sits on two corporate boards: The New York Times and Fanatics, the sports retailer that just accepted a mammoth investment from the Japanese conglomerate SoftBank. SoftBank is in talks to possibly obtain a substantial ownership position in Uber — and Khosrowshahi’s loyalties will be watched closely.
“I cannot think of a better choice for Uber,” said Doug Macks, the CEO of Fanatics.
Another tea leaf: Khosrowshahi has displayed some fascination with autonomous vehicles, a research priority of his predecessor, Kalanick.
Google driverless car. Finally I can text and drive! pic.twitter.com/gwu9GKrRWJ— dara khosrowshahi (@dkhos) October 22, 2014
Khosrowshahi could also satisfy rank-and-file Uber employees’ desire for a CEO who will fight the Trump administration. Publicly, Khosrowshahi has been critical of U.S. President Donald Trump, and his company joined early efforts to challenge the president's executive order targeting Muslim refugees and immigrants — an issue that some at Uber said Kalanick did not protest aggressively enough.
He himself is an immigrant who came to the U.S. from Iran when he was 9 years old, part of a wealthy business family, leaving in 1978 just before the Iranian Revolution.
“My father had to go back to Iran to take care of his father when I was 13 and was detained for six years before returning,” Khosrowshahi told Bloomberg. “My mom was raising three kids without a dad.”
Khosrowshahi has been married twice and has four children, said those who know him well, and spends a lot of time with his extensive family network.
He has also been politically active, supporting Democratic presidential candidate Hillary Clinton with a donation last year, though he has also donated to some Republicans.
And this past February, he ended a company earnings call with a direct shot at the White House.
“Hopefully we will all be alive to see the end of next year,” he said.
Additional reporting by Rani Molla and Tony Romm.
This article originally appeared on Recode.net.