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Monday, Oct 19, 2026

Uber CEO Spent Months Undercover As Driver And Delivery Agent, Here's What He Learned

Uber CEO Spent Months Undercover As Driver And Delivery Agent, Here's What He Learned

Mr Khosrowshahi's moonlighting was part of a campaign by him.
Uber CEO Dara Khosrowshahi recently revealed that he spent several months as the company's driver to understand the experiences of drivers during the pandemic. However, the experiment eventually forced the CEO to "reexamine every single assumption that we've made".

Uber CEO made dozens of trips as a driver in the following months ferrying people around the hills of San Francisco. Mr Khosrowshahi's moonlighting was part of a campaign by him.

In an interview with Wall Street Journal, Mr Khosrowshahi shared, "I think that the industry as a whole, to some extent, has taken drivers for granted." He used his experience as an undercover driver to make several important changes to the ride-hailing app

During his time as an undercover driver, he was punished by the app for rejecting rides, tip-baited by customers and faced several other challenges that helped him understand the issues that drivers face.

While sharing his experience as an Uber driver, the CEO said that he struggled to sign up as a driver, saw firsthand something called tip baiting and was punished by the app for rejecting trips. Surprisingly hard to take was the rudeness of some Uber riders.

The campaign-code-named Project Boomerang has helped shape what has become one of the biggest makeovers of Uber's business since its inception in 2009, reported WSJ. The CEO was under pressure from investors to increase profits.

Uber faced a labour shortage after the economy reopened in 2021. The company figured out that it had to do more to get drivers on board than just offer them bonuses. The company adopted some difficult changes that the drivers had asked for, and they paid off.

Uber's ride-share revenue more than doubled in 2022, and the company posted its first full-year adjusted profit since its founding. It now commands 74% of the U.S. ride-share market, up from 62% in early 2020, according to consumer receipts analyzed by market research firm YipitData.

Mr Khosrowshahi's said that "The whole experience was pretty clunky."

He began his stint as an Uber driver by using a secondhand Tesla to masquerade as an Uber driver chauffeuring people around the city, with a curated Spotify playlist and all.

Mr Khosrowshahi made him implement several changes, but he said that there is still a long way to go.
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