Jen Berrent was a WeWork lawyer and executive who left the high-profile startup about three years before its 2023 bankruptcy. She’s now CEO and co-founder of the legal startup Covenant, an AI-powered law firm tailored to private market investors.
The former WilmerHale partner talked to Evan Ochsner about the parallels between the impact of WeWork on real estate and AI’s ongoing disruption of the legal industry. Their conversation has been condensed and edited for clarity.
Q: What lessons did you take from WeWork?
There’s a lot of lessons from WeWork—there’s a new category of real estate. And it’s the same thing with law. We think there’s a legacy business, a slice of which could have a very different experience for clients, that can be made into a product, that doesn’t need to go to Big Law firms, but benefits from a whole different client experience. WeWork built on Zipcar. This had happened before in other legacy industries.
Q: How does your WeWork experience inform the way you’re funding Covenant?
We’re cautiously fundraising. We are more deliberate fundraisers, and we recognize that the amount of fundraising—even though companies think it doesn’t—does dictate your burn. And so, when you raise money, you spend more money, and that is important when you think about sustainability as a company. We are very strategic in how we think about fundraising in terms of capturing a market.
Q: Did your legal background prepare you to be a CEO?
There’s some of it that is more similar to when I was a partner at a law firm. I was a partner and I built relationships. Even though Covenant relies on tech to exist, it is still a relationship business, and because we’re selling to clients, there is still a large portion of my time that is spent talking to clients and building up that trust and building that relationship.
Q: What are the big differences you’re seeing between being a CLO and a CEO?
As the CLO at WeWork, the car was accelerating. My job was to make sure the road was paved, to make sure that a tractor trailer wasn’t coming out, to see around corners, and to really think about how you’re going to make it a smooth ride, and then, obviously, avoid trouble. And we had business troubles, but we had no legal troubles. Now I really need to think of that vision. I need to say, “This is where the car is headed, and this is where I’m going.” And it is a very different skill set thinking through this.
Q: Which job is more fun?
I was the general counsel at WeWork, and then I was the CLO at WeWork. There’s a lawyer part of me that loved being general counsel. I really did like that. This is more fun because it is seeing AI change the law, which is just super exciting.
