Jen Berrent, WeWork's 'legal mastermind,' has earned millions and survived executive shakeups. Here's how the loyal enabler of Adam Neumann became WeWork's most senior woman.

Jen Berrent, WeWork's co-president and chief legal officer, is the only senior woman at WeWork and the company's top legal executive. Current and former employees have described her as an Adam Neumann and WeWork enforcer, the legal mastermind who found ways to protect the company and its CEO, no matter what tricky situation presented itself. She was in the room for many of the coworking company's most critical meetings. One person described her role as one who handles everyday issues so that his boss doesn't have to, and in that sense said she is Adam Neumann's Michael Cohen.A spokesperson for WeWork declined to comment on behalf of both Berrent and the company.Adam worked closely with Jen for many years with great respect for her counsel and skills, a spokesperson for Neumann told Business Insider. She had responsibility for major parts of the company and was one of Adam's most trusted managers and advisors.For more WeWork stories, click here.Adam Neumann was screaming at Jen Berrent, the woman who had been, for the past five years, his closest company ally. The WeWork board had gathered on a late September day to force him to resign and he wasn't going down without a temper tantrum.Neumann was under a lot of stress. During a short-lived pre-roadshow for an IPO, the company he founded had been treated by institutional investors like a smelly box of compost; investors liked the general idea of the company but held their noses and their distance. No institutional investors were eager to buy the stock, as headline after headline documented the excesses of Neumann's leadership style, WeWork's partying culture, its odd governance structure and pages and pages of his alleged self-dealing disclosed in the prospectus.Neumann, who is dyslexic, relied on Berrent, the company's top lawyer, to oversee the hugely critical IPO prospectus. She wrote sections of the document that detailed controversial related-party disclosures, which some say she approved and, in other cases, masterminded. She, in turn, worked closely with then-CFO Artie Minson and outside counsel at Skadden, Arps, Slate, Meagher and Flom. People close to Neumann say, despite being the CEO, he never thoroughly read it.As WeWork's board forced Neumann to tender his resignation, he focused his anger and blame, as he had on Berrent and other executives many times before, full force on to his top lawyer, according to one person familiar with the matter.A spokesperson for WeWork declined to comment on behalf of both Berrent and the company.Adam worked closely with Jen for many years with great respect for her counsel and skills, a spokesperson for Neumann told Business Insider. She had responsibility for major parts of the company and was one of Adam's most trusted managers and advisors.A 'legal mastermind' who found ways to do what Adam Neumann wantedThe meeting was ugly, but in the end, Neumann stepped down and Berrent stayed. She remains at the company, a survivor in an otherwise broad house-cleaning of Neumann allies that occurred after he gave up control. These days, Berrent, WeWork's only female senior executive, is keeping a low profile. Employees haven't seen her name on an all-hands email for months, despite her position as one of the most senior members of the management team and former HR chief, and her reputation for inclusive meetings and inspiring speeches. She's still working daily, multiple people tell Business Insider, but in the background. She helped, for example, manage the company's 2,400 job cuts last month. Berrent's importance to WeWork cannot be overstated. In conversations with dozens of current and former WeWork employees, Berrent's name came up repeatedly. One person described her role as one who handles everyday issues so that his boss doesn't have to, and in that sense said she is Adam Neumann's Michael Cohen. Others described her as a Neumann and WeWork enforcer, the legal mastermind who found ways to protect the company and its CEO, no matter what tricky situation presented itself. Another stressed her loyalty, comparing it to that of a consigliere, a term sometimes used to refer to an adviser to the head of a crime family. Others pushed back on those characterizations, describing her as one of the most competent people at the startup, who balanced out Neumann. She was someone expressly focused on getting things done, who felt it was her job to orchestrate his wishes when the board approved them in ways that protected him and the company.What everyone can agree on is that in the last few years, Berrent played a critical role in advising Neumann on some of the embattled company's most unsavory issues. She's successful. She's smart. She worked for the guy, said one former executive. Her job was to execute what he wanted. This person described Berrent as world class at what she does. If she's directed by someone for good, she can be used for good.At WeWork, Berrent felt she could finally be her authentic selfBerrent's journey to WeWork's executive suite followed a much more traditional path than the larger-than-life Neumann, a child of a kibbutz and an Israeli Navy vet who founded WeWork after earlier startup attempts failed. She grew up on Long Island and traveled just 120 miles for college to the Ivy League's University of Pennsylvania. She attended the prestigious New York University's law school and three years after graduation, joined 100-year-old Covington and Burling as an associate. Two years later, in 2006, Berrent joined another prominent practice at Wilmer Cutler Pickering Hale and Dorr, rising to become head of the firm's emerging companies practice. In that role, she worked with up-and-coming startups like WeWork. One story goes that as part of her efforts to drum up new business, she camped out at a WeWork until she could introduce herself to Neumann. In September 2014, after Neumann personally recruited her for months, Berrent officially joined WeWork as general counsel. Two months later, it raised $355 million from T. Rowe Price, Goldman Sachs and Harvard at a $5 billion valuation. Berrent would play a key role in negotiating WeWork's later fundraising rounds. She told employees she felt that WeWork was a place where she could be her authentic self. When I left a law firm to join WeWork, I emailed my colleagues a farewell note, quoting E. E. Cummings: 'To be nobody-but-yourself-in a world which is doing its best, night and day, to make you everybody else-means to fight the hardest battle which any human being can fight; and never stop fighting.' I felt an urgency to be at a company where I did not need to fight quite so hard to be me. That place is WeWork.Berrent was the only senior woman at WeWork and felt women had to work ten times harder to reach the topIn the early days, Berrent and Neumann bonded during one-on-one meetings they held while walking around New York. As WeWork grew so did her stature within the company - Berrent worked long hours wearing many hats, including chief operating officer, that saw her act as WeWork's chief fundraising negotiator, lawsuit handler and Neumann confidant. Across a sea of white, male leadership, Berrent stood out as the only senior woman. She's also gay, married and raising two daughters and a son. In the early days, she used those non-traditional traits to appeal to a workforce that considered itself part of a cause larger than just leasing out coworking space. She had a speech which riled people up in a good way, one person recalled. If you feel like you've been an outcast, if you feel like you've been mistreated because you're a woman, because you're gay, whatever it is, I'm here to tell you We is your home.By 2016, she was running legal, marketing, events and HR, in addition to holding the title of chief culture officer. Increasingly, she was called on to handle personal situations for the Neumanns, as well as the company. When one executive, rising star and Berrent direct report, Will Potter, fell out of favor with Neumann's wife, Rebekah, over his opposition to one of her fads, Adam called on Berrent to dismiss him, according to a former colleague. Potter, who didn't respond to repeated requests for comment, left the company in May. Another described Berrent as having to babysit Neumann. Before the all hands meetings, it was clear that she'd have to spend all night at Adam's apartment while he was drinking tequila and dictating things, one person close to both executives said.Before the all hands meetings, it was clear that she'd have to spend all night at Adam's apartment while he was drinking tequila and dictating things.Berrent took her work seriously and felt women needed to work ten times as hard as men to reach the top, one person familiar with her thinking said. She didn't have patience for those who whined instead of working hard.Two days after her grandmother died, in 2017, Berrent boarded a plane to close one of WeWork's most important deals of all time, the initial $1.3 billion Softbank investment.With strong feelings of loss, I boarded an airplane for Japan to lead the most important negotiation of my career. Adam called with strategy, advice, and encouragement, and without an ounce of doubt in my strength, she wrote in a public post to the troops in 2018. In April 2019, Neumann reshuffled the executive ranks and stripped Berrent of her COO title. Instead, he made her chief legal officer and co-president. (The COO title was given to a London-based exec, who, by the time of the IPO preparation and WeWork's corporate entity shift into a C-structure series of LLCs a few months later, had drifted back into the background.) Minson, who later became co-CEO with Sebastian Gunningham, shared the president's title with her. Berrent's LinkedIn profile stands frozen from that time, listing her as COO, but there's also reason to believe that she maneuvered a way to keep the role. In August, as the march towards the planned IPO picked up, Berrent signed a new employment contract. While her formal title remained co-president and CLO, her new work contract called her Co-President, Chief Legal Officer, and Chief Operating Officer of the company.A loyal soldierGender, diversity and people issues would dog Berrent's time at WeWork.She personally approved the firing of at least one manager who had repeated HR complaints claiming disrespectful behavior toward women, according to one person familiar with the matter. Multiple employees also told stories of coming to her with ideas about improving WeWork's diversity hiring, after she had urged them to do so in her speeches, only to feel brushed off with a demeanor some described as cold, a potentially sexist label often attached to high powered women. She was prone to freezing people out once they stopped being useful to her, leaving a trail of former allies now essentially dead to her, according to two people who dealt with her. She kind of took this very lawyerly, legalistic view of things that people are out to screw you over and you had to protect yourself, one former colleague said. That was her default.Earlier this year, she was named as a defendant in a sexual harassment and gender discrimination lawsuit brought by Lisa Bridges, a former HR executive who reported to her. Bridges alleged massive differences in pay between men and women at the company, particularly when it came to equity grants, and said Berrent cut her out of key meetings after she raised concerns. In the complaint, Bridges pointed to equity grants that WeWork awarded in February, alleging that of the 61 employees granted in excess of $1 million only three were women.Two former WeWork execs told Business Insider they saw examples of gender pay imbalances, while two female ex-employees said they felt underpaid.Bridges also alleged that Berrent told her that men are paid more than women because, for example, men take risks and women don't and women are `second earners,' according to the complaint.At the time the complaint was filed, WeWork denied the lawsuit had any merit. Bridges later told the court that she dismissed her earlier claims. A WeWork spokesperson declined to comment on behalf of both Berrent and the company when asked about the allegations for this story.Berrent's sometimes ruthless work ethic can be seen in corporate documents she helped write.One of Berrent's jobs in her early days was formalizing employee roles and responsibilities. One clause, around non-compete restrictions for those leaving the company, drew the attention of New York Attorney General Barbara Underwood. Berrent had defended the clauses in 2017 by explaining Our people are our soul. But in September 2018, Underwood forced WeWork to scale them back because she saw them as too restrictive.Jen's a very compliant soldier to the point that her morality became secondary, one former executive said. It was hard for her.A multi-million-dollar reward for a job well doneBerrent has been handsomely rewarded for her work as Neumann's head enforcer. When WeWork issued multimillion loans to board members for buying their stock options, the company also granted loans ranging from $3 million to $6.3 million to Berrent, director Lew Frankfort, and Minson. The company then gave Berrent and Minson bonuses in the exact amount of their outstanding loans, which they used to pay off their debt, according to the S-1. She also has a generous exit package: if Berrent resigns in the first year after a change in control, she's entitled to a year's salary ($871,154). Under some forms of termination, she would be eligible for immediate vesting of outstanding equity awards, according to her employment contract. At the time of the S-1, she was set to get 347,424 shares over the next decade, though it's unclear if that still applies after SoftBank bailed out the company. These days, Berrent's job is fraught with complications. Lawsuits against WeWork, which Berrent must oversee, continue to pile up. The Securities and Exchange Commission and the New York State Attorney General are now investigating the company. Future lawsuits seem almost guaranteed. Such investigations don't usually reflect well on a company's top legal exec. On the other hand, Neumann's departure signals a fresh beginning. Berrent may compartmentalize the pain and move forward, current and former colleagues say. She just had this attitude that you suck it up and work harder, one former employee said, and you will get there.

Jen Berrent, WeWork's 'legal mastermind,' has earned millions and survived executive shakeups. Here's how the loyal enabler of Adam Neumann became WeWork's most senior woman.

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