The real reason a top Uber executive abruptly left shows how much mistrust and fighting there really was behind the scenes
- Uber's spectacular meltdown in 2017, full of executive departures, is well-documented.
- Business Insider has the inside story of how and why several key people in former CEO Travis Kalanick's brain trust really left.
- Read the full story: THE TAKEDOWN OF TRAVIS KALANICK: The untold story of Uber's infighting, backstabbing, and million-dollar exit packages
Rachel Whetstone's seemingly abrupt departure from Uber in April 2017 did not go unnoticed.
Whetstone, after all, was the embattled ride-sharing company's head of policy and communications. And Uber was in the center of the worst storm of bad press anyone in the business could remember.
But while her exit caught outside observers by surprise, it didn't come completely out of the blue.
Before Uber, Whetstone had served for years as head of public policy and communications at Google. Those years had made her rich, and when she arrived at the ride-hailing company, she wasn't under the spell of potential wealth, which drove other top players at Uber.
"That made her feel like she could speak truth to power with [then-Uber CEO] Travis," a former executive said. "She wasn't part of the group of yes-men who would never disagree with him."
Over time, Whetstone had become disillusioned with Uber. In her role as a powerful woman in the company, she was someone who many troubled employees and other insiders felt comfortable venting to. As these people shared negative stories with her, Whetstone began to see Uber differently. She became angry.
She saw a company that needed to grow up, but that under CEO Travis Kalanick, wouldn't.
As Whetstone became increasingly frustrated with Uber, she developed a reputation with some as being difficult to work with, becoming easily upset. She would threatened to quit, but would then cool down and change her mind. Or Kalanick talked her down and encouraged her to stay.
Kalanick indulged her at first, feeling she was a good resource for the company. But over time, he felt, she had become too much drama to deal with.
"She had this distaste for the company, starting with Travis," one person said, adding, "Rachel hated the company, but was there punishing the company for making her be there."
The time Kalanick accepted Whetstone's resignation
The situation came to a head after a damning article about Uber was published in the tech news site The Information.
The article described how a group of Uber executives - including Kalanick, his then girlfriend, Gabi Holzwarth, and business head Emil Michael - visited a South Korean karaoke bar in 2014. That bar turned out to be more like an escort service, featuring women with numbers taped on them.
Before Holzwarth talked to The Information, she reached out to Whetstone and told her that she had received a call from Michael. Holzwarth and Michael had been close friends when she dated Kalanick. Michael warned her that the press might start digging into the Korea incident. Holzwarth told Whetstone that she felt as if Michael was threatening her not to talk.
When the story came out, it included a reference to that phone call and portrayed Whetstone as being sympathetic to Holzwarth and asking her if anyone from Uber had expensed the night in the karaoke bar. The story also said that Whetstone had reported the call to the legal team, which turned the information over to Holder's investigators, citing someone "with direct knowledge of the matter."
Kalanick was not pleased. As his head of PR, he felt Whetstone was supposed to be defending the company from stories like these, not be part of them.
Not only was Whetstone doing a poor job of defending the company, Kalanick's inner circle believed, she was riling other employees and stirring up gossip. Kalanick talked to her about these concerns. The subtext was alarming: the implication that she was somehow the source of the negative leaks to the press.
Such intimations were both insulting and potentially career-ruining. A PR person found to be leaking would almost definitely never work again.
In early April, Whetstone quit. The next day, she changed her mind and said she'd like to stay.
This time, however, Kalanick accepted her resignation. Over dinner, they amicably negotiated an exit package involving millions of dollars' worth of stock that vested over time and agreed on a face-saving explanation that kept Whetstone on as a consultant.
On April 11, her resignation was announced and Kalanick publicly praised her as she left, calling her "a force of nature, an extraordinary talent and an amazing player-coach who has built a first-class organization."