Zenefits GC Joshua Stein On Outside Counsel, Moving Past Regulatory Challenges

Joshua Stein, Zenefits

Joshua Stein, general counsel for San Francisco-based human resources software company Zenefits, is half-coach, half-soldier. Literally.

Stein joined the Army in 1992, fresh out of college, looking forward to a 20-year career complete with what gets shown in commercials jumping out of airplanes, running around in the woods, firing off weapons systems, he said. But a drawn-down army, lessened in ranks following the end of the Cold War, Stein said, proved less exciting.

So, after four years of being a soldier, he became a coach. Or a ski instructor, at least, in Colorado.

Then, inspired by his uncle, a criminal defense attorney, Stein went to law school.

More than 15 years later, Stein has served as a judge's clerk, an assistant U.S. attorney, a senior associate at Quinn Emanuel Urquhart & Sullivan, an associate general counsel for private military company Blackwater USA and general counsel at OptumRx.

In 2015, he joined Zenefits as its general counsel, but was promoted to chief compliance officer in February 2016, in response to the company's insurance licensing scandal. Some of the company's insurance sales reps were found to be unlicensed in violation of the law in California and other states.

In the wake of the scandal, former chief executive Parker Conrad was ousted, scores of employees were let go and incoming CEO David Sacks promised a new company.

Stein helped the company settle with multiple states' insurance departments and, in November 2016, became GC again.

The Recorder recently sat down with Stein to discuss his company's response to its licensing issues last year, project management and leadership skills, and what Stein values in outside counsel. The following interview has been edited for clarity and length.

The Recorder: How big is the legal department?

Joshua Stein: [We have] 14 positions, 10 are filled and we're hiring for four. It's [all] legal and compliance. The legal folks are all lawyers. There's no paralegals, no assistants, no overhead like that. It's six lawyer positions and eight compliance positions.

TR: That's a beefed up compliance team. Has it always been that way?

JS: No. Our first full-time compliance positions started in February 2016.

TR: And it was a response, essentially, to the firing of Parker Conrad and other regulatory issues?

JS: Yes, it was. That's when I was named chief compliance officer. That was the first compliance position. But it's also something that's driven [our company]. Our product is highly regulated and covers such a broad waterfront. Benefits both insurance and noninsurance [are] complexly regulated on state and federal level. Payroll complexly regulated, with tie-ins on regulations on federal and state level. And then HR and employment again, highly complex, both federal and state components so, our folks are not just compliance like you think about in companies where they focus on the company's behavior. Here, they're very much focused on product, and that's part of what makes it so fun to work here as a legal compliance professional. You have really deep input into the product.