Career Lessons from Judi Hart: Business Decisions Impact People

E​arly last year, Judi Hart’s career took an unexpected turn. After almost two decades in HR, she became chief operating officer (COO) at PEAK6, a Chicago-based investment and technology firm with 1,200 employees. Previously, Hart had served as the organization’s chief people officer.

On the surface, the shift may seem momentous—but Hart doesn’t see it that way. As COO, she says, she applies the same critical lesson she learned in HR: “There’s not a single decision a business leader makes that doesn’t have a people impact.”

After Hart joined PEAK6 in 2018, its portfolio of companies increased from two to six in her first year. Each of those companies had its own siloed operations—its own HR, legal, finance, marketing and IT teams, among others. Meanwhile, PEAK6 gradually expanded Hart’s responsibilities beyond HR to include marketing and facilities. In 2020, PEAK6 centralized its operations and placed them under the purview of Hart, its first COO.

Hart’s people-oriented perspective serves her well in her current role. “I’m really strong at leading a diverse group of people to deliver,” she says. “I don’t need to be an expert in finance, compliance, legal or marketing if I’ve surrounded myself with the right group of people.”

Those who have worked with Hart also believe the COO position is a good fit for her. “I was not surprised she took this bigger role on the operational side,” says Cory Randles, people business partner at Apple in Culver City, Calif., where Hart worked as an HR director for four years before joining PEAK6. “More than a lot of HR people I’ve worked with, Judi really tries to understand the business problems that need to be solved. She has a great gift for bringing people together to drive change.”

As the tumultuous events of 2020 unfolded, Hart used what she calls her “wartime leadership skills” to help quickly steer PEAK6 operations from almost entirely in-office to almost all remote when the pandemic hit. As employees’ work and personal lives overlapped in multiple ways, “we as leaders had to be more empathetic and compassionate,” she says. She helped guide the company through a period of heightened social unrest, for instance, by giving people time off to participate in protests.

The company had created her role just in time. “I couldn’t fathom going through what we went through in 2020 without having a central leader who brought all the teams together,” she says.

‘Wrangling Crazy’

Just as her HR expertise has informed her work as COO, Hart says, a commonality across the companies where she has worked has similarly primed her for her current role. “They are all organizations led by passionate, creative leaders who have very big personalities and who want to disrupt industries,” she says. And each of the companies was on the verge of explosive growth when Hart arrived.

Early in her career, she worked as an HR manager and generalist for video game developers Mike Morhaime and Frank Pearce at Blizzard Entertainment. Later, as vice president of people and culture at Beats by Dr. Dre, she worked closely with company founders and music industry executives Jimmy Iovine, Luke Wood and Andre “Dr. Dre” Young. Now, at PEAK6, she reports to founders Jenny Just and Matt Hulsizer.

To collaborate with “absolute visionaries,” as Hart describes them, she keeps her emotions in check and brings a level-headed attitude. Hart sees her role, in part, as translating the founders’ vision to the employees who work to achieve it.

“I don’t want to alter their brilliance, but my job has been to take that, absorb it and not react to it,” she says. Put another way, “I always jokingly say my job is to wrangle crazy.”

Hart recalls interviewing for the position at Beats. “Luke Wood clearly told me, ‘I’ve never known my HR person and never really wanted to, so I’m not even sure how to hire for this role,’ ” she says. Hart thought to herself, “Challenge accepted.”

With Hart’s guidance, the organization grew from 25 to 750 employees, then integrated with Apple while maintaining Beats’ strong culture. Less than three years after she joined the company, Hart remembers, Wood was asked about the most impactful thing he did at Beats. His reply? Hiring the right HR leader.

Blending Candor with Compassion

Just as important as her relationships with founder-leaders are the ones Hart forms with employees. “When I take a minute to … ask about people’s kids and their weekends and keep a sense of humor, I build relationships with them,” she says. “And when I do that, people work that much harder. People really aren’t that high-maintenance. A little bit of care goes a long way.”

Her approach blends candor with compassion. “I’m clear, direct and transparent,” Hart says, “but I’m also kind in my delivery. My intent is always to help.”

Former colleagues can attest to this. “She’s direct with heart,” says Denise Dunlap, who has known Hart since 2003, when they both worked in HR at what was then Vivendi Universal Games (now Activision Blizzard). “She’s a straight shooter, but people don’t leave conversations thinking they were disrespected.”

In 2005, Dunlap hired Hart to help her build the HR function at Blizzard Entertainment. Today, Hart’s former boss happily reports to Hart at PEAK6. “I knew nothing about the firm except that Judi believes in it,” Dunlap, the company’s chief people officer, says of joining the organization two years ago.

For Hart, her success at founder-led organizations has hinged on her ability to identify the kind of employee who thrives there. Hart neatly characterizes the type: “Their life is work and they love it, but they also have a sense of humor, which is important when you work the way we work.”

Hart may as well be describing herself. “I get a lot of joy and passion out of work,” she says. “I always have.”

Integrating Work and Life

In fact, work has been part of Hart’s life since she was a teenager. She went to a high school in Austin, Texas, that had a business co-op program, where she attended class for half the day and worked the other half. It then took her eight years to graduate from college because “I chose to work full time and go to school part time,” she says.

To get her degree in music at the University of Southern California (Hart wanted to become a radio DJ), she first had to complete an internship. As an older student with her own apartment, she balked at the idea of working as an unpaid intern.

So, to fulfill the requirement, she landed a paid job as a recruiting coordinator at Vivendi Universal Games. “And I fell in love with HR,” she says.

While Hart’s career thrived, she eventually ran into challenges related to what she calls “work/life integration, not work/life balance,” when she experienced a major change in her personal life. In 2006, Hart had her first child, and she was wracked with doubt: “Should I stay home or work? Am I a bad mom? Am I a bad employee?”

She decided, at first, to stay home. Less than a month later, she took on a contract recruiting gig. “It was about staying connected with who I am, using my brain and having something outside of my child,” she explains.

In 2008, 21 months after the birth of her daughter, Hart had another. “It was the hardest thing I ever did, having two kids,” she says. “And it immediately sent me back to work.”

Hart returned to the workplace full time. Yet she learned she couldn’t let her job wholly dictate her sense of worth. That had led to constant self-doubt. “I spent years consumed by what others thought of me,” she says. “I gave so much of my power away to the job.”

So, Hart decided two things. First, it was perfectly OK in work settings to admit any knowledge gaps. “I allowed myself to say, ‘I don’t know, but I’m super resourceful and I’ll find out,’ ” she says. Second, Hart released herself from the hounding fear of losing her job. Now, she says, “I fundamentally believe I’m employable, and either the place I’m at sees that value or they don’t. And if they don’t, I believe there is someone who does.”

That fear of unemployment had its roots in Hart’s childhood—and it’s entwined with her tireless work ethic.

Both of Hart’s parents grew up very poor on farms, picking strawberries and cotton. “That’s what drove them, and I was raised with that,” says Hart, who has an older brother and sister. Hart’s father later started his own investment firm; her mother worked as an executive assistant. 

As her parents’ fortunes rose, the family moved into a nice house near a country club. But her mother tried to “keep up with the Joneses,” Hart says, and Hart’s parents eventually filed for bankruptcy. “The next thing I knew, all five of us were in a one-bedroom apartment,” she says.

“If you ask me what drives me today to be the person I am and work the way I work, it’s that experience,” she says. “I have two daughters, and I don’t want that experience for them.”

Even so, Hart has learned in recent years that life doesn’t have to play a subordinate role to work. She owes that lesson to PEAK6 co-founder Just, a working mother of four. “She’s the most successful female I’ve ever met,” Hart says, “and because she operates the way she does, she has given me the flexibility to do the same.”

Pre-pandemic, Hart planned flights for business trips so she could get home in time for her kids’ plays and basketball games. She never misses any of their events. “[My boss] taught me that I can have professional success while putting my family first,” she says.

Novid Parsi is a freelance writer based in St. Louis.