Uber’s CEO Worked as a Driver for Months. Here’s What He Discovered.

After focusing on the customer experience for many years, the company wanted to take a turn in the driver’s seat

Dara Khosrowshahi, CEO of Uber, arrives at the Sun Valley Resort for the Allen & Company Sun Valley Conference on July 05, 2022
If you live in the Bay Area, this man may have hoisted your luggage in the last few months
Getty Images

Last year, Uber experienced a slowdown in driver recruitment. So CEO Dara Khosrowshahi decided to secretly sign up as a driver in September 2022 to better understand their experiences. It was part of an initiative to get drivers back on the app called “Project Boomerang.” It seems like two main themes arose while picking up passengers around San Francisco for several months: the Uber app is super frustrating for drivers to use, and people are really mean.

Khosrowshahi purchased a used grey Tesla Model Y and joined Uber as a driver under the alias “Dave K.” Things were rocky from the start. First off, Khosrowshahi had trouble with Uber’s sign-up process, saying it was difficult to navigate. He also said that the hard-to-use interface made it hard to transition from one fare to the next. To add insult to injury, the app punished him for rejecting particular fares. And, in a point that comes as no surprise, Khosrowshahi said that the fear of a lower rating gave him something akin to the Sunday scaries.

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“One passenger recognized the Uber CEO and asked for advice on his startup,” reported The Wall Street Journal. “Mr. Khosrowshahi said most riders haven’t recognized him, though, and have collectively given him a five-star rating. He said he gets nervous the nights before he drives, out of concern that his rating might dip the next day.”

Although most passengers gave him a good rating, Khosrowshahi said that when people would discuss personal problems or confidential work information in the vehicle he was driving, it made him feel disrespected, as if the passenger felt they were the only person in the car — almost like he wasn’t real. The CEO also made food deliveries riding an electric bike and said that rampant “tip-baiting” was also an issue. This is when customers say they’re going to give the delivery person a big tip before they arrive, then reduce it after delivery, which is a terrible thing to do. 

While Khosrowshahi can’t possibly understand the financial burden that many of these drivers likely face, it certainly made for an interesting experiment that will hopefully improve the app for drivers — and possibly open some riders’ eyes to the rude things they’re doing, if they even care.

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