Plan Insurance Blog

Uber CEO Turns “Undercover Boss”

Dara Khosrowshah takes a reality ride through into the gig economy.

After a half-decade as the boss of Uber, CEO Dara Khosrowshahi decided to do what he’d never done before… drive for Uber. His experience is an interesting insight into how the tech innovator’s high-level policies impact on the day-to-day workings of the gig economy.

Let’s put this experience into context by looking at the challenges Uber has experienced over the last few years. The ride-hailing behemoth has been battling a shortage of drivers and delivery workers. As we’ve said previously in the Plan Blog, without an army of drivers waiting in the wings for a job, Uber’s business model begins to look unsustainable.

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To counteract this, Uber has been performing a balancing act. The struggle to provide cheap enough rides to the public, while still adequately paying their workforce and sustaining a costly corporate operation has not been an easy one to overcome. A big chunk of Uber’s expenditure has also been poured into projects like self-driving cars, which have so far proved little more than costly experiments.

Adding to this mix are Uber’s ‘legal hurdles’. This is the phrase the Wall Street Journal uses to describe Uber’s ongoing compliance battle. Uber recently spearheaded a whopping $224 million campaign in favour of Prop 22, a law that enabled companies in the gig economy to continue treating drivers as independent contractors in California. The outcome of Uber’s worker status confrontations in the US remains unsure.

Dara Khosrowshahi goes undercover as Dave K

As covered in the Wall Street Journal, Dara Khosrowshahi recently decided to go undercover as an Uber driver and Ubereats delivery driver under the inventive name ‘Dave K’.

Although it’s great fodder for the media, It’s objectively a pretty busy bizarre situation.

He’s been spotted driving someone to the airport, getting stuck in Oakland traffic, curating Spotify playlists, and even forgetting someone’s drink (this caused him to realise a flaw in the app design, so contacted an executive to change it).

He even admitted something that will have Uber drivers throwing their hands up. Khosrowshahi said that it’s not ideal to have no idea how much you’re going to be paid or where you’re going before accepting a ride. This is something many Uber drivers have been complaining about since the app was first created.

A Time Honoured PR Play

Khosrowshahi is not the first tech CEO to don the driver’s hat. Lyft CEO John Zimmer and even Uber’s former CEO, Travis Kalanick did it too.

It’s a tried-and-true great marketing tactic that top executives have been doing for years. The new CEO of Starbucks, Laxman Narasimhan, said in a letter to employees he plans to work at Starbucks stores every month. It’s great for PR, and it’s good for showing employees that you’re just one of them.

The problems that Khosrowshahi experienced as a driver make this situation slightly more interesting. Khosrowshahi, despite leading Uber for five long years and positioning drivers as ‘its customers’, hadn’t personally navigated the customer experience until now.

The Human Element of Driving

Many would argue that since Uber’s inception, the humans involved in their day-to-day business have been treated merely as stepping stones to the future. I am, of course, talking about driverless cars. Back in 2015, former CEO Travis Kalanick envisioned a future with robotaxis, with Google, Tesla, and Apple all fighting for a piece of the action.

In 2019, Elon Musk attempted to fully automate the Model 3 factory, only to realize that it was a no-go. The takeaway? Musk put it perfectly, “Humans are underrated.” Khosrowshahi voiced a similarly significant realization to the WSJ, “I think that the industry as a whole, to some extent, has taken drivers for granted.”

Maybe this admission was the byproduct of his recent jaunts as a driver. Maybe it was just a moment of sober reflection. Whatever the case, it’s a stark reminder that even in a world fueled by algorithms and apps, the human touch is still invaluable. And as long as that holds true, there will be a need for the Dara Khosrowshahis of the world to take a dive into their day-to-day reality of their business.

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