Alexander sued Whetstone but lost

In September 2018, Eric Alexander filed suit against Rachel Whetstone, alleging that she had violated a reciprocal non-disparagement clause in her severance agreement with Uber. In particular, Alexander alleged that Whetstone spread false, misleading, and disparaging information about Alexander’s response to the rape in India — which he says were the cause of his termination from Uber. Alexander also accused Whetstone of making a variety of racist comments, claimed that Whetstone incorrectly asserted he stole the rape victim’s medical file and bribed Indian authorities to get that file, and claimed that Whetstone said she would “ruin [his] career” by telling investigator Eric Holder about supposed misconduct.  Alexander argued that these statements were false and defamatory.

Whetstone argued, among other things, that a severance agreement required all disputes to be resolved through arbitration, not litigation. The court granted her motion to compel arbitration. In February 2023, the court entered judgment for Whetstone.

Kalanick criticized SVP Whetstone for reporting escort bar visit to investigators

After Uber then-CEO Travis Kalanick and colleagues visited an escort bar and tried to cover it up when asked, one person who had been there contacted Rachel Whetstone, then Uber’s senior vice-president of communications and public policy, seeking guidance. Whetstone in turn reported the matter to Uber’s attorneys, who turned it over to Eric Holder, who was at the time investigating possible improprieties at Uber.

Business Insider described Kalanick’s response:

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.

BI continued, explaining how some at Uber saw Whetstone as “difficult to work with … or even irrational,” but others saw her “speaking truth to power”:

One employee described her as “intellectually honest.” Whetstone was already rich from her years at Google and 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 Travis,” a former executive said. “She wasn’t part of the group of yes-men who would never disagree with him.”

For her part, 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 stories with her, Whetstone began to see Uber differently. She became angry.

She saw a company that needed to grow up, but that under Kalanick wouldn’t.

Ultimately Whetstone resigned and Kalanick accepted her resignation. BI reports that Whetstone’s exit package included millions of dollars worth of stock as well as keeping Whetstone on as a consultant to save face.

Escort bar visit cover-up

Uber employees visited a South Korean escort bar.

When one member of the party later complained, Uber SVP of Business Emil Michael contacted Gabi Holzwarth (who had been dating Kalanick at the time) — asking that she tell anyone who asked that it was just karaoke. She refused, taking his request for a cover-up as impetus to discuss the incident publicly.

Details from The Verge.

Mike Isaac’s Super Pumped (p. 305) reports that after Michael contacted Holzwarth, he alerted Uber SVP of Communications Rachel Whetstone who consulted with general counsel Salle Yoo and others — all hoping to conceal the situation so it wouldn’t leak.