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Empathy. That’s the first word that comes to mind when Geoff Mathieux, cofounder and CEO of ride-hailing company Wingz, thinks of Uber’s potential new CEO Dara Khosrowshahi. 

“He’s known to be fair and nice,” said Mathieux, who has personally met with the former CEO of Expedia dozens of times at conferences and when Expedia invested millions into Wingz. 

Fair and nice is the antithesis of Uber’s former narrative. Cofounder Travis Kalanick repeatedly skirted the law as he grew the company into a tech giant valued at $70 billion with millions of users. Khosrowshahi will need to drive Uber out of a PR nightmare with its toxic and cult-like internal culture, mismanaged relationships with drivers, legal battles across the globe, disgruntled and fighting investor group, and ongoing lawsuit against Google. 

Khosrowshahi’s also not afraid to speak out against things he does not support, such as President Donald Trump and his actions in the office. 

Uber’s former CEO Travis Kalanick agreeing to serve on Trump’s advisory council was one of the actions that led to the #DeleteUber movement earlier this year. 

Uber did not respond to a request for comment. Neither the company nor Khosrowshahi has publicly spoken out about the hiring. According to several reports, Uber offered the position to him but he has not accepted it, yet. 

In the meantime, people are gushing over the dark horse candidate. The New York Times cast him as a man who loves his parents. Recode wrote that he “spends a lot of time with his extensive family network.” 

Running Uber is not just about playing nice guy, of course. 

Khosrowshahi also will need to manage the company’s financial losses and potentially steer Uber toward an initial public offering. Luckily, he has a deep knowledge of running a big business successfully. He is credited with pushing Expedia to rapidly grow in revenue and in profit, despite the financial crisis and the competitive landscape in the travel industry. 

“Desperation sometimes drives innovation,” Khosrowshahi told Financial Times in a recent interview. 

He led several acquisitions and investments over his 12 years at Expedia. For example, Expedia bought vacation rental company HomeAway as well as Travelocity and Orbitz in 2015. 

Khosrowshahi also is quite familiar with the ride-hailing industry via an investment. He chose for the company to invest in Wingz, a ride-hailing app where all rides are pre-scheduled and users can choose to book the same driver every time. 

“Our drivers are waiting for you, rather than you waiting on the curb for Uber and Lyft,” Chris Brandon, who previously served as CEO of Wingz, told Mashable earlier this year. 

“Expedia owns a part of Wingz, and he was the person who made it happen,” Mathieux said. “They spent three months doing due diligence, looking under the hood.” 

He also personally invested in Convoy, a competitor to UberFreight, Recode reported. While he may now have to divest his shares, it does prove he has some knowledge of the industry. 

One of the most contentious parts of Khosrowshahi joining Uber is that he will be replacing the founder and CEO Travis Kalanick, who was ousted in June by the company’s investors. “TK” was worshipped by many of the company’s more than 15,000 employees. 

But this isn’t Khosrowshahi’s first rodeo growing a company he didn’t create. He joined Expedia as CEO two years after founder Richard Barton stepped down. Erik Blachford, formerly president of Expedia North America, served as CEO in between the two. 

And he’s got the look.

When it comes to managing the board of directors, Khosrowshahi also has a leg up. Benchmark Capital, one of Uber’s largest investors, reportedly backed Hewlett Packard Enterprise CEO Meg Whitman, according to Recode. Fortunately for Khosrowshahi, Expedia founder Barton is a venture partner at Benchmark. 

Khosrowshahi will need to prioritize re-staffing or re-shuffling the executive team below him as well. Over the last six months, ever since former Uber engineer Susan Fowler Rigetti published her explosive blog post exposing the company’s toxic work environment, more than a dozen Uber executives have fled or been forced to resign. 

Image: bob al-greene/mashable

In addition to the internal issues, his team will have to face the other big players in the ride-hailing industry, including the number two in the United States Lyft and the other players abroad. 

Khosrowshahi is quite familiar with fierce competition. Expedia is up against Airbnb, other travel websites, and any other tech giants that would consider venturing into travel logistics. 

“Amazon is a company that you have to take very, very seriously,” Khosrowshahi said at the 2016 GeekWire Summit. “We can’t control what Amazon does, what Google does, what Facebook does. What we can control is building incredible experiences and services for consumers.”

As Uber CEO, that mission hasn’t changed. 

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