In episode 10 of GC Sidebar, Andrew Epstein, General Counsel at Demandbase, joins host Trista Engel for a sharp conversation about innovation, leadership, and the unconventional paths that shape a legal career.
From rethinking how legal teams embrace AI to reframing strategy so it resonates across the executive table, Andrew shares how he’s working to break the “office of no” stereotype and empower his team to lead with creativity. He reflects on career-defining moments, from a law school internship with the Washington Nationals to navigating a complex corporate transaction at LiveRamp, and opens up about the unexpected passions, like spoken word poetry, that have influenced his journey as a lawyer and leader.
Prefer reading over watching? Below is the complete transcript from our GC Sidebar interview with Andrew Epstein, General Counsel at Demandbase.
Trista Engel:
Hi, I’m Trista Engel, CEO of Paragon Legal, and welcome to GC Sidebar, a short and sharp conversation series with today’s most forward-thinking general counsel. In just four questions, we cover the legal industry, leadership, careers, and a little fun.
Today I’m joined by Andrew Epstein, General Counsel at Demandbase, an enterprise software company that helps B2B teams focus their sales and marketing efforts on the accounts that matter most.
Andrew began his legal career at O’Melveny & Myers and tested the in-house waters as a secondee to Morgan Stanley. Before moving in-house to LiveRamp, rising to Head of Legal, he stepped into his first general counsel role at Demandbase in 2021.
But if we go back a little further than his time at O’Melveny, his legal career started a little more major league than most, with a dream law school internship for my hometown baseball team, the Washington Nationals, where he continued to work throughout his 2L year.
Andrew, I’m glad you’re here. Thanks so much for joining me.
Andrew Epstein:
Thank you for having me. Love the intro.
Trista Engel:
Let’s dive in. What’s the biggest challenge facing GCs and in-house legal teams today?
Andrew Epstein:
I think the biggest challenge facing GCs and legal teams really is twofold. It’s the ability to keep up with innovation and this perception that lawyers are not able to do so and are not creative, and are going to be the factory of no, or the office of no.
One thing that we do on our team, particularly as it relates to AI, is challenging the team. I manage commercial, privacy ops, customer trust, and governance, risk and compliance. I’m really pushing the team on what is a repeatable process you do all the time that you’d like to not be doing, that you think you can use new technology for. How do you push yourself to be innovative as a member of the team to help fight that perception, or that misconception, that legal isn’t able to do those things?
Trista Engel:
I love that. That is definitely something that’s a common theme , legal is slower to adopt technology, slower to move, slower to innovate , and you’re actively fighting that perception by really encouraging your team to fly in the face of it.
What’s the most valuable lesson you’ve learned as a GC?
Andrew Epstein:
As a GC, one of the most valuable things you don’t realize right away is that you’re in this unique role amongst the executive team, and sometimes the board, where folks don’t necessarily have a strong opinion or perspective on how you run your organization.
People will have opinions on a sales strategy or a marketing strategy or profitability versus growth, but they don’t necessarily have a strong opinion on how to run a legal team or legal strategy. So if you need to get something across, you have to be able to frame a key initiative in a way that’s impactful to the listener, and makes sense to them, depending on who they are, in order to move your agenda forward.
That comes into play when you’re arguing a position for a certain product perspective, or going to your CFO to get budget, explaining why legal ops is so important, for example. People are not always going in with preconceived notions, so you have to figure out, who is my listener and how can I frame this argument to get my point across?
Trista Engel:
That’s a really interesting observation , people spend more time thinking about the marketing strategy and the sales strategy than they think about the legal strategy. In some ways that’s a good thing, giving you more leeway, and in some ways it forces a different level of communication, education, and convincing that others don’t need to do.
Andrew Epstein:
Yeah, and it also serves this alternative role in the sense that people start to view you not just for your legal opinion, but for your opinion across other things, and how your perspective can help frame their initiatives and help move them forward.
Trista Engel:
What’s one career moment that changed your trajectory?
Andrew Epstein:
The first was very early days in law school. I think it’s a very traditional route in your 1L year to clerk for a judge, then get your law firm summer associate gig. I knew that wasn’t something I wanted to do. I didn’t want to be a litigator, so I waited until the week before finals to get my 1L summer job, which was stressful. But I landed this gig at the Nats, and I actually took that job part-time throughout my 2L year as well.
Being able to work in a GC’s office, see a ton of different things, and work at the baseball stadium was a really unique opportunity that opened doors for me.
The second was when I was at LiveRamp. We went through this really interesting transaction in which we spun out and sold our parent company and fellow subsidiary to a quasi competitor. We de-listed from NASDAQ, re-listed on ICE, and had a kind of mini IPO. I was working closely with our GC at the time, but for part of the transaction I was running it on behalf of legal. It was a massive, unique deal. Coming out of it and running the US legal team at LiveRamp gave me the confidence to take the next step into the GC role.
Trista Engel:
What’s something people watching might not know about you?
Andrew Epstein:
I used to run a spoken word poetry event at UC Berkeley, and I was part of the collegiate poetry team there that went to nationals. I started watching Def Jam poetry when I was a kid on HBO, got interested in it, joined the team at Berkeley, and then created this event to raise money for breast cancer. It ended up being a really successful event, and I did it all four years at Berkeley.
Trista Engel:
That is so cool. What a great endeavor and a great fun fact.
All right, the bonus question , who is your favorite fictional lawyer?
Andrew Epstein:
I think I’m going to knock this one out of the park, because it’s a fictional lawyer and also not a lawyer , Mike Ross from Suits, who is both a real lawyer but also on the show not a real lawyer.
Trista Engel:
You nailed it. I haven’t gotten that response yet. Love it.
Well, that was really fun, Andrew. Thank you so much for sharing your journey and your insights.
Andrew Epstein:
Thank you. Thanks for having me.
Trista Engel:
All right, that’s a wrap on today’s episode of GC Sidebar. Catch more great conversations on our website at paragonlegal.com. Thanks for tuning in.
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