Illustration by John Hemminger

Driving Uber forward: Inside CEO Dara Khosrowshahi’s quest to transform the company

Dara Khosrowshahi enters a small conference room in Uber’s Toronto office, greeted by a dozen drivers, keen for access to the ride-hailing company’s top executive. All but one of the “driver partners,” as they’re officially called, have worked with the company for longer than Khosrowshahi, Uber’s self-described “rookie” CEO. The new leader wants their insight on how to make the company better.

“This has been the craziest year for me professionally,” says Khosrowshahi. The former Expedia CEO joined the ride-hailing company in the wake of a scandal-plagued 2017 that saw Travis Kalanick, the company’s co-founder and then-CEO, pushed from the helm. “The company had come to an incredible place as far as creating an innovative service that I think most cities in the world want and need now,” he tells the drivers. “But also, I think we grew too fast. And along with that hypergrowth, we made our share of mistakes.” Moving on will require working with the people in this room, and others like them.

The roundtable, part of Khosrowshahi’s first visit to Canada as CEO, is in keeping with the company’s 180 Days of Change initiative, a listening tour launched in June to get driver feedback, and a nod to the company’s newfound efforts to improve transparency and culture as it matures—perhaps belatedly—from its startup to its legacy phase. In the year since Khosrowshahi’s selection, the CEO has overhauled Uber’s power structure, reducing voting rights of Kalanick and early investors on the board. He ended forced, confidential arbitration in cases of sexual misconduct, involving employees, and he rewrote the company’s values. As Khosrowshahi puts it, he’s introduced “adult supervision” to a company built on the popular startup philosophy of “move fast and break things.”

Talking Point

On his first visit to Canada as CEO—a year after taking the reins of the company then in crisis—Khosrowshahi sits down with The Logic to share his views on taking Uber from a ride-hailing company to a multimodal transportation business. To do so, the company will have to regain trust from disgruntled cities and forge new relationships with competitors and even old rivals.

As Uber gears up for an IPO next year, however, culture is just one factor being rejigged to ensure the company’s success over the long term. “We want to take Uber from a car-hailing service to a transportation service,” Khosrowshahi said during an address at the Toronto Region Board of Trade last Thursday—a message he conveyed repeatedly throughout the day. The ambition involves putting masses of e-bikes and scooters on the roads, partnering with public transit authorities to solve “the last-mile” problem and building out the company’s self-driving car capabilities—the reason for Khosrowshahi’s Toronto visit, where he announced a $200-million investment to expand Uber’s autonomous-vehicle development lab, which will boost the company’s Toronto workforce from 200 to 500 in the coming years.

Khosrowshahi is under no illusion that Uber will achieve all that single-handedly; it will require partnering with cities, other companies and even old rivals. “This is a $6-trillion transportation [market] we’re going after,” he says when we meet at a downtown Toronto restaurant during his whirlwind stop in the city. “Ultimately, we want to debundle all the use cases for car ownerships, especially in urban destinations. And we’re not going to be able to do it all ourselves.”

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