Uber boss became a driver to see what drivers really go through

Uber boss Dara Khosrowshahi was under pressure to increase revenue from the ride-hailing app in the wake of the global pandemic, which brought the overall economy of the United States to a screeching halt, but boosted the gaming economy to such an extent that Uber could not meet user needs. Uber needed more drivers, and fast, but the company’s resistance to classifying drivers as workers and a wave of complaints related to Uber the app’s notoriously poor design — for drivers, that is — held it back.

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The tech company’s CEO concluded that the best way to solve Uber’s driver-related problems was to get behind the wheel of a car and become an Uber driver yourself, which The Wall Street Journal reports in a lengthy profile of the “undercover boss.” Khosrowshahi allegedly bought a used Tesla Model Y in a very safe, but very boring, gray paint job, and ferried riders around San Francisco (where Uber is based) for months under the alias “Dave K.”

Khosrowshahi began collecting fares in September 2022 as part of an ongoing campaign called “Project Boomerang”, which aimed to improve Uber for drivers rather than riders, and therefore entice more people to start driving for the service. It’s not just about a first-class experience exclusively for riders, but also for drivers.

But the start was far from premium for Khosrowshahi, who struggled to navigate Uber’s registration process and later had hopes of receiving generous tips dashed by the common practice of “tip baiting.” The Uber app penalized the CEO for rejecting certain fares, and the clunky interface made navigating and transitioning from one ticket to the next difficult.

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In other words, the app sucks for drivers. Khosrowshahi’s ride also showed him what it’s like to be at the mercy of rider reviews, according to WSJ:

A passenger recognized the Uber CEO and asked for advice on his startup. Mr. Khosrowshahi said that most riders have not recognized him and that they have collectively given him a five-star rating. He said he gets nervous the nights before he drives, worried his rating might drop the next day.

But WSJ says that the CEO’s months-extensive experience, culminating in just 100 trips and deliveries, has led to the company’s biggest makeover since 2009. The company’s annual results also benefited from Uber reported higher revenues and profit in 2022 than previous years.

Funny that it would take the Uber CEO and a handful of other executives to get behind the wheel, and experience the technical difficulties and stresses drivers face firsthand (as well as the rudeness of Uber riders) to change things.

I encourage you to read the whole thing WSJ profile, because it’s about as close to a benign parable about the tech industry as we’re likely to get — especially when it’s about the CEO of a company like Uber, which has been at odds with its drivers (ahem, workers) for years.

The experiment is far from perfect, and is hardly representative of what the average Uber driver (who doesn’t happen to moonlight as the CEO of a major tech company) will go through. At one point, for example WSJ says the CEO vowed never again to pick up a ticket that would take him over the Bay Bridge to Oakland during rush hour. How many Uber drivers can say the same without facing any kind of monetary loss?

But the profile at least shows how doing things that benefit those who actually do most of the work can have positive effects on the company’s bottom line. Rather than trickle down, this is trickle-up economics at work.

The changes to the app that the CEO’s driving days brought are being praised by drivers who have long called for similar changes and more transparency in pay. Now maybe let’s give these slightly happier Uber drivers some significant benefits, and not just app updates or UI updates.