Uber CEO reveals his nightmarish experience while moonlighting as an Uber delivery driver

In a recent interview with The Wall Street Journal, Uber CEO Dara Khosrowshahi said his most nightmarish experience with the company occurred when he moonlighted as an Uber delivery driver. It wasn’t the riders that were an issue for Khosrowshahi but rather, the logistics of delivering food.   

“I was trying to deliver food and I couldn’t find where to drop it off,” Khosrowshahi said. “Trying to figure out the maze of apartment complexes was a challenge.” He continued, “The most fun was delivering food to a touch football game. I was like, ‘Where’s the building I’m supposed to be delivering to?’ It was a field. There was a bunch of dudes.”

Khosrowshahi’s stunt, which took place last September, was part of an effort to understand why the company was seeing a dip in driver recruitment at the time. The CEO himself came face-to-face with a series of challenges that drivers endure on the daily. There’s the faulty location systems, which make it especially difficult for drivers to navigate large apartment complexes. There’s the slimy practice of “tip-baiting,” where customers promise couriers with large tips only to reduce them after the delivery is made. And, of course, there’s boisterous and inconsiderate riders.

In his interview, Khosrowshahi added that improving drivers’ work conditions starts with corporate Uber employees “using our products” and “getting in the shoes of a driver.”