In a highly anticipated announcement, Uber Technologies Inc. has selected Dara Khosrowshahi, CEO of Expedia Inc., as its new CEO, The New York Times reported on Sunday. The choice of Khosrowshahi to replace ousted chief executive Travis Kalanick comes at a time when life at the San Francisco-based company isn't exactly a joyride.

In the last 12 months alone, Uber has had to contend with sexual harassment and discrimination allegations, hire two law firms to conduct parallel internal investigations into company culture and engage in a high-stakes legal battle with Google Inc. division Waymo over driverless car technology. And as crisis after crisis has unfolded, a slew of executives have left the company.

Now that a CEO has been named, additional hires may be made in the very near future. Many sources said they expect the general counsel seat, vacated when former GC Salle Yoo was promoted to chief legal officer in May, to be one of the next positions filled.

From conversations with dozens of recruiters, legal consultants, outside counsel to Uber, former in-house counsel and candidates for in-house employment, Corporate Counsel learned of a legal department that has been demoralized, with one former in-house counsel sharing that their colleagues had less faith in Yoo following the firing of two attorneys earlier this year.

A Very Private Law Department

The company is shrouded in secrecy, a familiar tactic for Silicon Valley companies that admire Apple Inc.'s approach to press communications, which includes tightly controlled external messaging and a company-first mentality from employees.

All visitors to the ride-hailing giant's San Francisco headquarters are required to sign nondisclosure agreements to set foot inside, even California regulators meeting with Uber's attorneys, public records show. Outside counsel often explain they cannot be quoted in articles that even mention Uber by name. And in-house counsel often lock up, even when asked to discuss seemingly innocuous news.

This secrecy can make it difficult to get a clear picture of what the legal department looks like and how it operates. But combing through LinkedIn profiles and state bar records of current in-house counsel has shed some light on this very closed-off legal team, which, according to Yoo's statements at a recent panel, has around 230 attorneys. Though not every lawyer at the company could be identified through these methods, Corporate Counsel has managed to learn a great deal about the makeup of the department.

For instance, in hiring in-house lawyers, it appears Uber has favored Harvard Law School, UC Hastings College of the Law, Columbia Law School and UC Berkeley School of Law graduates. The company also looks often to firms Covington & Burling, Littler Mendelson and Morrison & Foerster and companies such as Visa Inc. and Apple when hiring for the legal department.

The average tenure of the current in-house lawyers at Uber is about 22 months, according to an analysis from Corporate Counsel using data found for lawyers with the company as of Aug. 24.

Getting Out

High on the list of priorities for the incoming general counsel could be hiring to fill the more than 30 legal positions at the company that are available globally, as of late August. These positions include associate counsel and counsel for transactions, senior counsel on privacy, a legal director for ethics and compliance, one legal analyst for labor matters and a couple of claims advocates.

LinkedIn data shows the company has had its fair share of departures in recent months. Some lawyers have stayed local with higher-profile in-house gigs at Square Inc. and Facebook Inc., and others landed in other cities at smaller, lesser-known companies such as Scopely Inc. and IMC Construction. Meanwhile, some have gone back to such law firms as Fenwick & West and Morrison & Foerster.

Of those who remain, some have been looking to get out, sources said.

One former Uber attorney, who spoke on condition of anonymity to preserve relationships within the company, said colleagues have expressed concerns about the department's leadership.

Many lawyers at the company, according to the source who left the company voluntarily earlier this year, have been disappointed by how things have changed, particularly in recent months.

This year got off to a rocky start after two in-house lawyers were fired by Yoo, as first reported by tech news website The Information. According to the report, the pair of lawyers, who were not identified by name, turned to outside counsel for advice, without the necessary authorization from Uber, about changes to the company's data and document retention policy that were proposed by Yoo and associate GC Angela Padilla.

In a meeting of members of the legal department the following week, the former in-house attorney interviewed by Corporate Counsel said there was a lot of confusion about what happened to the fired lawyers.

After the incident, Yoo “vaguely described what happened,” the source said. “She didn't name the two attorneys but we know who they are. … Both people were highly respected. … They were hardworking, serious attorneys.”

The attorneys were so highly regarded that “a chunk of the litigation team left in protest,” according to the former in-house lawyer.

“That broke a lot of the trust we had in the general counsel,” the source said.

Based on LinkedIn profiles, at least seven of Uber's litigation counsel appear to have changed jobs since the start of the year. These lawyers did not respond to requests for comment, so their exact reasons for leaving are unclear.

This is a sizable portion of the litigation group, judging by numbers on one Uber lawyer's LinkedIn page. Lindsey Haswell, former litigation director and now regulatory director, shared on her profile how she built a team of litigation personnel that grew from two to 20 people from 2015 through early 2017. (Haswell did not respond for comment for this article.)

Of the departing litigators, the lawyers had been with Uber for less than 18 months, on average, and left for a mix of firms and other in-house roles, according to data gathered by Corporate Counsel. The longest tenure among attorneys in the group was 28 months.

One former in-house attorney has come to the defense of the top lawyers in the department. The source, who spoke on condition of anonymity and did not have direct knowledge of the two lawyers' termination, said at Uber, “I always felt encouraged, and indeed required, to speak up about concerns and to always do the right thing. Salle Yoo is a person of the highest ethical character, as is Angela Padilla.”

After the two in-house attorneys were fired, morale took another hit in February when former Uber engineer Susan Fowler published a blog post painting the company's workplace culture as toxic. Fowler made claims of rampant discrimination and harassment at Uber.

“It was really upsetting,” the former in-house lawyer who left earlier this year said of reading the post. “It's certainly what everyone was talking about on Monday. … We were instant messaging, emailing about it internally.”

With some scandals reported in the press, that source said, employees would shrug it off as “our current enemies trying to get us.” But the ex-Uber lawyer said the Fowler allegations were taken seriously.

But even before 2017, in the last year to two years, some lawyers who joined the legal department quickly left, said Julie Brush, founding partner of the California-based recruitment firm Solutus Legal, who based her information on the nature of her job and interactions with lawyers in the community.

Brush said the reasons for leaving are unique to each lawyer and vary from lack of cultural fit to what some job seekers see as a dearth of growth opportunities within the legal function.

And in some cases, it may just be that recruiters are “calling people at Uber with a lot of amazing opportunities,” she added.

Growing Pains

The former in-house lawyer said that many of the internal problems at Uber were a direct result of growing pains within a company on an upward growth trajectory.

Yoo is the first to admit that it was difficult to prepare for Uber's quick rise.

Yoo started with the company as its first in-house lawyer in May 2012 as Employee 102. The company, which was most recently valued at nearly $70 billion, now has more than 14,000 employees, according to a June email sent to staff.

In an August 2016 American Bar Association meeting in San Francisco, Yoo noted that back in her early days in 2012, there was not “a single piece of litigation” on her desk.

In the legal department's infancy, Yoo turned to generalists to fill out the legal team, according to an interview with the ACC Docket, and moved to a “specialist model” as issues became more complex.

Yoo did not personally respond to Corporate Counsel's requests for comment for this article.

In other efforts to deal with growth, Yoo attempted to layer strategically, which wasn't well received by all team members. Yoo explained in her interview with the ACC Docket how she “would start by hiring high-level people first and let them hire a team.”

For one of the lawyers who spoke to Corporate Counsel, the swift changes within the legal department were jarring and inadvertently created silos. As the source recalls, the changes, even as recently as moving from 2015 into 2016, were challenging.

“It seemed like a completely different legal department,” the former Uber lawyer said of the transition period when the size of the department nearly doubled.

Whereas lower-level attorneys were once frequently in the same meetings as the general counsel, from 2016 onward, that was not the case. Face time with the GC, according to the source, became increasingly rare.

“I get that as you grow, you have to add hierarchy,” the former lawyer said. “It was at a degree that was unexpected.”

Apparently Yoo acknowledged the silos within the department to her legal team, but the source “never saw any plan or any attempt to rectify that at an institutional level.”

Despite the ups and downs within Uber's legal department, not everyone is trying to get out.

“I'm proud of the people who are still there,” the source said. “We had some rocky times.”

Brush, too, said despite quick departures for some attorneys, the number of people looking to leave has recently tapered off somewhat. “There's a little bit of a wait-and-see attitude because the company is trying to replace a number of executives,” she offered as one reason why this may be the case. “And there are a lot of new lawyers to replace the ones that have left and to hire new head count.”

A Hard-Driving Work Environment

For the lawyers who are opting to stay, their workload might not be getting any lighter, in the near future anyways.

Yoo makes it routine to come into the office every Sunday just to avoid being interrupted by nonstop meetings, she told the ABA last year. She even gave up playing tennis after coming in-house because she doesn't have the time to dedicate to such activities outside of work. She said she does commit to cooking dinner at home on Tuesday nights, but even then, her husband and kids can expect her laptop is out and she's on call for work.

“It's all one life,” Yoo said last year of work-life balance. “I can't say 'after 6 [p.m.], no meetings.' It doesn't work that way. That's really when [Asia Pacific] APAC is really getting going.”

In a July 28 deposition in the case of Waymo v. Uber Technologies, Kalanick, the former CEO, said it is the norm for certain Uber employees to work well past midnight. In fact, he said he wished working such late hours was “more routine” at the company.

Moving Forward

Yoo's successor won't have it easy.

An early test for the new general counsel will be how he or she handles Uber's battle with Alphabet Inc. driverless car division Waymo, which is set to go to trial in early October. Waymo claimed in a Feb. 23 complaint that former manager Anthony Levandowski downloaded more than 14,000 confidential files and then formed his own self-driving car company called Otto, which Uber acquired in August 2016.

As of Aug. 24, Uber was named in 82 open complaints in all U.S. district courts, including 28 complaints in California, with 27 in the Northern District of California, home to Uber's operations. On the district court level, Uber is the plaintiff in just one open matter, a lawsuit filed against a John Doe plaintiff that Uber claims was the source of a 2014 data breach.

Yoo's successor is also expected to help implement the 47 recommendations made by Covington & Burling, based off the firm's internal investigation into Uber's workplace culture, and to handle a criminal probe by the U.S. Department of Justice into Uber's “Greyball” program. The New York Times, which first reported on the program, said Uber uses Greyball software to evade law enforcement and public officials in cities where it has received regulatory pushback. The Times' report noted that the legal department, led by Yoo, approved the program.

Despite these challenges, some would surely jump at the chance to take the general counsel job. Former Takata Corp. GC Eric Laptook said in a July interview with Corporate Counsel he “wouldn't hesitate for a moment” if asked to be Uber's new GC. Several in-house counsel and former general counsel told Corporate Counsel that Yoo's replacement would have the opportunity to help turn the company around, build a new corporate culture and work on novel legal issues.

But one veteran GC who has worked at several technology companies and who requested anonymity to maintain current working relationships in the legal industry, said the open GC role might not be all it seems to be on paper.

The open position in this case, the former GC said, still reports to Yoo, and might not have as much freedom as a typical general counsel, who interacts frequently with the board of directors.

“That's a red flag,” said the veteran general counsel in a recent interview. “I don't have any inside knowledge of the issues at the department, but it seems the person responsible for building it up is now walking away from it and handing the reins to someone else for day-to-day management.”

The incoming Uber GC's relationship with Khosrowshahi may also be very important.

As The Information pointed out in May, Yoo, who was general counsel at the time, had little control over what Kalanick did when it came to messaging to staff about the Waymo case. Not long after Waymo filed the complaint, Kalanick reportedly told employees in a staff meeting that they had looked at everything and determined that the company did nothing wrong.

Yoo, according to the article, later told Kalanick in an executive meeting that his comments were irresponsible because Uber had “not done what you said we did” in terms of carefully looking through the facts.

It's true that with Kalanick out as CEO, a new GC may have more control, but at least part of Uber's success relies on the fact that the company operates in what are sometimes grey areas. It remains to be seen whether this will ultimately change with a new CEO, making room for the legal department to more carefully consider and dictate the company's next moves.

Contact Stephanie Forshee at [email protected], David Ruiz at [email protected] and Jennifer Williams-Alvarez at [email protected].