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Ep 107: From Big Law to GC Before 35: Andrew Epstein’s Journey on Navigating Modern Legal Careers
55 Plays6 days ago
In this episode of The Abstract, host Tyler Finn sits down with Andrew Epstein, General Counsel of Demandbase, for a candid conversation on building a legal career rooted in curiosity, intentionality, and creative risk-taking. From starting his career in the GC’s office of the Washington Nationals to handling high-stakes spinouts at LiveRamp, Andrew shares how he made bold choices, built trust across functions, and scaled legal teams strategically. He dives deep into building legal ops, leveraging AI thoughtfully, and what it really takes to thrive as a first-time GC. A must-listen for in-house leaders, aspiring GCs, and legal professionals navigating a rapidly evolving legal landscape.
Read detailed summary: https://www.spotdraft.com/podcast/episode-107
Topics
Introduction – 00:00
Andrew’s intentional path to law school and first job at a GC’s office – 02:28
Working for the Washington Nationals and using that experience to stand out – 04:38
Choosing O’Melveny for its cross-office structure and California links – 08:10
From Capital Markets to Privacy: Why Andrew Left Big Law for In-House at LiveRamp – 09:49
Managing complex transactions: M&A, spinout from Axiom, NYSE listing – 17:18
Privacy, Adtech, and Proving Your Value in a Changing Legal Team – 22:04
Getting hired as GC at Demandbase through cross-functional trust – 27:33
Scaling the legal team intentionally for IPO readiness – 29:41
Growing as a first-time GC through peer mentorship – 32:43
Building a lean, flexible team that integrates AI and legal ops – 35:35
Encouraging AI experimentation over shiny tools – 40:08
Rapid-fire Question – 46:04
Connect with us:
Andrew Epstein - https://www.linkedin.com/in/andrew-epstein-3b22a471/
Tyler Finn - https://www.linkedin.com/in/tylerhfinn
SpotDraft - https://www.linkedin.com/company/spotdraft
SpotDraft is a leading contract lifecycle management platform that solves your end-to-end contract management issues. Visit https://www.spotdraft.com to learn more.
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Transcript
Navigating Workplace Politics at LiveRamp
00:00:00
Speaker
So like at one point you're negotiating, it's going to stay at live ramp. What's going to go to axiom. And I'm negotiating against my boss's boss who ultimately like have the ability to, I guess, fire me. So like that structure doesn't work. Cause I'm like, I'm like pushing hard for live ramp against this person who is in my org. it was just very odd. And I think that that's so interesting. Yeah.
00:00:24
Speaker
At what point we like had this other lawyer come from Axiom to LiveRamp to help the LiveRamp side. And he we were on a call together and we would be advocating for LiveRamp. And he would be saying like,
00:00:34
Speaker
um
00:00:37
Speaker
on the call, the brother's like, Andrew has no idea what he's talking about this. And I like that. No idea what he's talking about. then he would mute and be like, you're totally right. I totally agree with you, but I got to take the other side on this. Like, what the hell, you know?
Introduction to Andrew Epstein's Career
00:00:52
Speaker
How do you chart a path to general counsel before the age of 35 while staying open to reinvention, learning to navigate different company cultures, and managing through massive industry shifts?
00:01:08
Speaker
Today on The Abstract, I am joined by my friend Andrew Epstein, General Counsel of Demandbase, where he leads the company's legal, trust, governance, and ops teams.
00:01:21
Speaker
His career has spanned big law, some big transactions, and multiple in-house roles, all grounded in a sort of mindset of curiosity, intention, and ownership.
00:01:35
Speaker
We're going to talk today a little bit about some of the career bets that he made early on, how he built credibility quickly, and what it means to lead legal today in really fast and changing market.
00:01:50
Speaker
Andrew, welcome to this episode of The Abstract. Thank you for having me, Tyler. I'm i'm pumped. I've been ah been listening for a while, so I'm glad to be on it. Yeah. I mean, I know you've got a lot of friends who've been on. Andrew Woods is a great episode um as well.
00:02:06
Speaker
We're going to beat him today, though. We'll we'll get more listens, I think. Yeah. Andrew Woods and I have a running competition on another podcast, so he's beating me on that one. So I'm coming for him on the abstract.
00:02:19
Speaker
Well, I mean, I can put a little bit of ad spend behind it. You know, I... There you go. Jokes aside, uh, you know, I don't actually start every episode with, with folks journeys through law school, but you were really intentional about, where you went to law school and and the sort of approach that you took then but some other decisions while you were there.
00:02:44
Speaker
I think it's useful. I think there are actually some folks who are listening who are thinking about if they should should go into law and and trying to make some decisions like that. um How did you approach the decision to
Influence of Personal Life on Career Choices
00:02:54
Speaker
go to law school? And how do you think that that that choice influenced your sort of early trajectory? Yeah, I mean, I think when I was at undergrad at Berkeley, I kind of knew pretty early on that I wanted to go to law school. The question was, you know, what would that germy look like for me? And I think... um I took, ended up graduating Berkeley semester early. And so in three and a half years, for personal reasons, actually, my mom at the time had gotten really sick. I grew up in LA. And I went down to take care of my mom. And I had taken year and a half kind of between school. I went and worked for nonprofit. They have unlocked for breast cancer, actually, where my job was like,
00:03:43
Speaker
like be a walker coordinator. I was literally signing people up to the San Francisco walk, helping them on their journey, helping them fundraise, doing a bunch of cold calls. Um, and so, um, That has helped me in my career, like the, you know, working kind of like Avon Walk. I worked at Nordstrom's kind of these like service industry jobs, but I knew that I wanted to eventually and go to law school. And when I was doing that, I knew that I wanted to be on the East Coast east coast for the first part of my career, specifically in New York. And so was pretty intentional about...
00:04:14
Speaker
And going to the best law school on the East Coast, which at the time that what I got into was GW. And so I made the decision to go there. I know it's not New York, but I knew that it was a good feeder into um the work, New York firms and firms and other type of work in New York.
00:04:30
Speaker
And I knew there would be like unique opportunities there in D.C. as a law student. So that's kind of what led me on that on that path.
Internship at Washington Nationals
00:04:38
Speaker
You did actually take advantage of sort of unique opportunities in in D.C. I think, you know, most folks after their first year second year, you know, they're thinking about government sort of internships, big law.
00:04:52
Speaker
um You went in-house with the Washington Nationals for the summer. That's pretty cool. i Tell us about how you got that opportunity and how it ended up sort of shaping your your journey then later in in law school.
00:05:08
Speaker
Yeah, I mean, I think, and that's part of you know, I think what you and i will talk about in a little bit is kind of taking a risk and taking a non-traditional path. And it's very traditional as a first year law student to, you know, a couple months in, there's an on-campus kind of recruiting thing where you go and mostly go and clerk for a judge. And there's no no knock for people to go and clerk for judging. Like, that's amazing.
00:05:29
Speaker
I knew I didn't want to do that. And so the question was like, what would I do if you don't sign up for something like that? You kind of have to apply to a bunch of things over time. And you're coming towards your the end of your one oh year. It's pivotal that you get an internship.
00:05:41
Speaker
And I didn't have anything until weeks before finals, honestly. And my friends had gotten things. And I knew i i was holding out because I had herded this job kind of like towards the back half of the the semester.
00:05:53
Speaker
And I got an opportunity to ah interview with the GC, this guy, awesome guy named Damon Jones at the time of the Washington Nationals. And I knew it was going to be really competitive. I went in to the interview and I just talked about why I wanted to be in the office of a GC, in a GC's office.
00:06:12
Speaker
Obviously, being at a baseball team is amazing. But I think a lot of folks before me, and I know this is Damon, told me this, went in and talked about how much they love baseball and like this guy's batting average and their favorite player and this and that.
00:06:24
Speaker
And it's like, you're not interviewing to be a scout. Like you're interviewing to be a lawyer, right? So I talked about how I thought in this three-person legal team that I had a ah an opportunity for a lot of impact and to see a lot of unique things. And that obviously resonated with him. And I got that job.
00:06:41
Speaker
And I was full-time my 1L summer. And then my two all year, I basically took a lighter course load and worked Mondays and Fridays. um at the Mets office, which was super cool because the office was at the stadium. And so specifically like for day games, you would go out and watch the last three innings, you know, on the clock, which was a good thing to do.
00:06:59
Speaker
That's awesome. ah Do you feel like that experience helped you stand out at all then when you went to interview for sort of like big law opportunities? I mean, i imagine there can't be that many folks walking in the door with ah office of the GC at a and a baseball team on their resume.
00:07:17
Speaker
ah Yeah, certainly. I think I absolutely think it did. um i I did well in school. i was not the best student coming out of GW, but I think um I did well enough to get a few interviews at ah on-campus recruiting at the time.
00:07:31
Speaker
And I do think part of that was i had this different thing on my resume that I could talk about. And again, it was like, how do you talk about that? Yes, that got you into the door, but I didn't just like, maybe I talked about baseball for 30 seconds of it or something, but then I actually talked about what I learned and what I did.
00:07:46
Speaker
And um it gave me this opportunity to go and and get my first, my 2L summer associate job, which was the job that ended up taking after school um at O'Melven and Myers, um I think in some ways because ah my interview stood out, you know, for for my background and kind of like how I, the type of work that I had managed, you know, pretty early on in my legal career.
00:08:11
Speaker
I think you were also pretty intentional about picking a firm like O'Melveny, or you had slightly different criteria than maybe other folks. Was just sort of like, how can I pick the firm that has the you know top starting salary? um Tell us about why you chose O'Melveny in New York.
00:08:29
Speaker
Yeah. Again, so I knew I wanted to be in New York. I knew ah grew up in LA. I went to um undergrad in the Bay. and knew I was most likely going to head back to California at some point, but I wanted to start my career in New York for a number of reasons. um One, i think i was I learned pretty early on in law school that I did not want to be a litigator. And I think that law school really trains you to be a litigator. There's not a lot of classes that you can take or opportunities that you get where you're more of a corporate or a transactional attorney, then that certainly was more of the corporate transactional side.
00:09:05
Speaker
Obviously, you can take contracts and some VC classes and um you know there's there's there are business law, there are opportunities like that. um But I knew i wanted to start in New York.
Choosing O'Melveny for Career Growth
00:09:17
Speaker
I knew that I wanted to work for a firm that had offices all over the country, particularly that was LA or West Coast based, which on Melbourne is Um, and that would give me the chance to work with partners, um, in the LA office and the SF office and the London office and the New York office so that I can diversify my practice, but also have my hooks into, um, California kind of when I knew that there was going to be here the high likelihood that I'd want to return.
00:09:49
Speaker
What did you end up focusing on in your practice? I mean, I know, you know, eventually you sort of bought a practice around privacy or or data. um But yeah, what was it like in the early days and there? and And how did you sort of diversify the different practice areas you were working on as well?
00:10:05
Speaker
Yeah, I actually didn't really start the privacy work until I i moved in-house. it was Oh, interesting. At the at the tail end um of O'Melveny, I did, but privacy wasn't really a thing and then. I mean, it was just starting to become a practice in these law firms. And I worked on the privacy front in the last maybe a year before I left. I worked for this honestly genius partner who i think ah so she has since left.
00:10:29
Speaker
She was um the GC of healthcare company for a while. i don't I don't know where she is now. i haven't even probably told her like how how impactful she was to me at the firm, but um she was just so smart. And I love working on the few projects that she had for me. She came on to help build the privacy practice in 2016.
00:10:48
Speaker
um But before that, I was working mostly for the capital markets group and some M&A work. um And again, that was somewhat intentional, right? You had 16 people in our summer associate class. And Melvony was known and is known as a litigation powerhouse.
00:11:05
Speaker
They were building out the transactional group and the capital markets group in New York specifically. They had poached this company. kind of Rainmakers type partner um from Sherman and Sterling.
00:11:19
Speaker
And he was building out the group and I hitched kind of my wagon to my, his name was Mike to Mike and his team. And I wanted to become in that summer.
00:11:32
Speaker
And then I want to become Mike's guy during that summer. And, so um out and cause he got kind of like the selection of summer associates. And, and when I joined Melvini, I was working on his deals, but it also with the nature of transactional practice,
00:11:50
Speaker
capital markets practice. We did a lot of bank side work, some issuer side work, IPOs, follow-ons, secondaries, things like that. But there is there are these ebbs and flows because you're you're either on a deal or multiple deals or you're not. And so I knew it would give me the opportunity to say, hey you know hey, Mike, can I go work for so-and-so partner in the SF office on one of his deals or her deals? Can I work on so-and-so partner in the LA office?
00:12:16
Speaker
And that And it was great. Sometimes it it ended up biting me in the ass, frankly, because like I would be on an l LA deal, a New York deal and a London deal at the same time. And like sleeping during that period is challenging. yeah,
00:12:34
Speaker
It also ah allowed me, you know, to go home l a to see friends and family and be able to be in an office. The same with my girlfriend at the time, wife now is from the Bay. um And so I'd be able to go to San Francisco and kind of do that work.
00:12:48
Speaker
um But i I kind of centered it around like, what are these smaller practices where I could have... an impact and not just be just another person or another kind of cog at the firm, a large firm.
00:13:04
Speaker
um And so when I approved myself to to Mike and to David, who was another partner there, who I'm very much as a mentor and a friend, um they allowed me to run deals much earlier on than I think I would have gotten at some of these more traditional,
00:13:22
Speaker
um transactional powerhouse firms where there's more of wait your turn type of approach.
Transition to In-House Legal Role
00:13:31
Speaker
What was it that motivated you to want to go in-house then? ah Besides the fact that in retrospect or in hindsight, you got to work with Vanessa Wu, another podcast guest who's amazing. And I'm sure that was an incredible experience. We can talk about that. But what was it that made you think, OK, I want to go in in-house and and try that side of ah practicing law?
00:13:54
Speaker
Yeah, I knew um as much as I like the work and and in the capital markets group, capital markets certainly like during that time is very much precedent based. Like what are other people in the space doing? What other risk factors are companies listening out in this space?
00:14:11
Speaker
Do your research. You know, there's rules there's very kind of set rules. I... i I've always liked to like color outside the lines a little bit, I think. And it was hard for me to um build my practice out of something that was so rigid.
00:14:29
Speaker
um And so I kind of knew I wanted to be more creative. i wanted to have this opportunity to impact a business um beyond just legal and sort of kind of set ah set your own kind of rules. um And that's why I started the the privacy work with one of the partners there.
00:14:46
Speaker
um Because it was 2016, 17, GDPR wasn't even out yet. And this concept of privacy as a company was pretty new. At that time, i had been going back and forth to California a bunch, and I knew I wanted to move back to the to the Bay, either LA or the Bay at the time.
00:15:03
Speaker
And I had asked a Melvini to transfer me and to San Francisco. And they were just, to the transfer was taking time at the same time I was applying to in-house roles from New York.
00:15:14
Speaker
um I almost worked for another podcast, Adam Greenberg at Warby Parker. I love that guy. That's a good episode too. Yeah, really good. These are all the hits. Yeah. um But I interviewed with Vanessa at LiveRamp to be the second attorney under her at liverap LiveRamp. LiveRamp at the time was a subsidiary of a public company called Axiom.
00:15:39
Speaker
which is 40, 50-year-old Arkansas-based data broker. um They had a acquired LiveRamp, which is very much the startup tech company based out of San Francisco, ah run by really smart guy, Travis May, at the time, and who had hired Vanessa to be the GC of LiveRamp. And so this was an opportunity to work for her.
00:15:59
Speaker
um and so this the timing worked as such that like I had gotten the offer... at live ramp the same day, honestly, or almost the same day as I recalled that my transfer had finally gone through at El Melviny. And so I had been asking them like, you know weeks separate. Where's this transfer going? What's going on transfer? How come this isn't going through yet?
00:16:20
Speaker
And then they were like oh, finally we figured it out. I'm like, oh, just kidding. i actually am leaving the front and I'm going to go start at this.
Major Transactions at LiveRamp
00:16:29
Speaker
uh data company and um in san francisco and i think a couple the partners the one who i worked for like totally got it he wished me best i still keep in touch with them a couple of other partners were like what are you doing ah this is a huge mistake that you're making really interesting yeah and i ah said i appreciate your
00:16:54
Speaker
you know, thoughts on that. I've enjoyed working for you. I want to take a risk here and um, I think it's going to work. And so, yeah, moved, moved to San Francisco and work and got the opportunity for work for Vanessa at this high growth subsidiary of a, of a public company where they really kind of like left this alone for, for a while.
00:17:18
Speaker
I know that you ended up working on it and she and i we danced around this a little bit on our episode ah because we mostly focused on sort of her experience at Rippling and some of the acquisitions that LiveRamp had done.
00:17:30
Speaker
um But you got to work on some pretty complex transactions while you were there, right? i mean there's a sort of like delisting from NASDAQ that happens, spin out from Axiom. um Can you walk us through a little bit about like what those deals looked like? And did you feel totally like comfortable doing that with the sort of capital markets background or is it very different in-house?
00:17:53
Speaker
um Yeah. What's the adjustment like to to in-house life? Yeah, I think there are some deals. I remember at the time had done a few more tuck-in transactions where we had done smaller, to $150 million.
00:18:07
Speaker
acquisitions or more of an acqui-hire type motion. And that I did feel more comfortable with. We worked with a really smart chief strategy officer there. And I did take the reins, again, a kind of mostly from Vanessa on that one, where I would work on those you know due diligence interviews, kind of the founders, and work with the deal team on that, work with post-transition integration was also a huge thing. I think so many companies think about it acquisition, but not about like the deal memo or the deal philosophy and what you're going to do after this deal is closed and how are you going integrate this totally different company, including systems, customers, contracts, all of these things. And so that, I kind of like had a baseline understanding of the transaction
00:18:54
Speaker
where LiveRamp sold Axiom, the parent company. I don't think anyone could have had the like background for that one. It was such a unique deal in the sense that um what ended up happening is like we were selling our parent, but we were sitting under...
00:19:13
Speaker
Like my boss's boss, Vanessa's boss, was that was the work for Axiom. So like at one point you're negotiating, what's going to stay at LiveRamp? What's going to go to Axiom? And I'm negotiating against my boss's boss who ultimately like have the ability to, I guess, fire me. So like that structure doesn't work because I'm like i'm like pushing hard for LiveRamp against this person um who is in my org. It was just very odd. And I think that- That's so interesting. Yeah, it was- I think that um at what point we like had this other lawyer come from Axiom to LiveRamp to help the LiveRamp side, and he we were on a call together, and we would be advocating for LiveRamp, and he would be saying, like...
00:19:56
Speaker
um no way like on the on the call the but i' saying andrew has no idea what he's talking about this and i i like no idea what he's talking about and then he would mute and be like you're totally right i totally agree with you but i gotta gotta take the other side on this like the hell you know but we ended up basically selling, selling our parent. And a lot of what was really interesting about the deal was how do we build the systems and infrastructure live ramp in a really short period of time. Like this deal was closing October.
00:20:25
Speaker
to best Vanessa was out in the beginning of it and then, and then back to help close the the deal. And um she, and she was instrumental and we worked a ton together during that time to, to close the deal in October of 2018.
00:20:40
Speaker
te we got the opportunity to go to the New York Stock Exchange. We had delisted from NASDAQ. We had listed on NYSE and, um, be there for the bell ringing, which was so cool. Um,
00:20:52
Speaker
um And so that's like the glamour of it, but but the behind the yeah scenes of it is like we had no contract management system at LiveRamp because we relied on our parent. um There was contracts that were coming over that were 10 years old, that were in PDF, that were not readable.
00:21:08
Speaker
We had to figure out which customers went where Axiom ended up being one of our biggest customers at the time because of how the deal works. So a lot of what I was doing was this like intercompany agreement work.
00:21:20
Speaker
What's going to stay? What's going to leave? How are we going to sign up our own contract management system and be able to run as an independent business come October 2018 when sign the close? And.
00:21:32
Speaker
the close um And then it was like team building because we had to bring over, we had to figure out some folks from the Axiom side on the legal side were going to go to IPG, which is where we sold Axiom to.
00:21:46
Speaker
And some folks were going to come to LiveRamp to work for us. And so just like the team dynamic, how we separated that out um and how we became an independent business during that time was super unique, really interesting transaction um and something I feel like very thankful to be a part of.
Privacy Expertise Development
00:22:05
Speaker
Where was it in this journey also, I guess, that you started to pick up privacy expertise or that that you felt like this is a place that i should I should really lean in? Because I know that ends up becoming huge part of what you do at Demandbase as well. i'm Curious to hear about that.
00:22:22
Speaker
Yeah, I mean, I think truly like at the outset of joining LiveRamp, that was just so core to the business. like I joined in 2016, I think, or 2017, and that was right before GDPR. We needed to make it very material changes to the business through GDPR, through CCPA, just based on what LiveRamp does.
00:22:43
Speaker
And um the privacy team was run separately, and so it didn't roll up to... um Vanessa at the time. And i think that um I've taken some learning from that and building my own team at Demandbase from a structure standpoint. But um We worked quite a bit with the privacy team i'm just given the nature of the business. So I feel like I don't, I did not, and I do not hold myself out to be a privacy expert, but I think you really have to understand privacy in the ad tech space um and currently in the in the go-to-market or the martech space, just given the type of work that we do.
00:23:23
Speaker
you always have to be kind of like, have enough knowledge to be dangerous. But I think you also have to understand Where are your, where do you need to help someone to come in and help you um kind of like bolster that knowledge so that you, who's going to, who's going to compliment you so that you know that you have built out the right team and the right foundation for the, for the work that you're doing?
00:23:46
Speaker
One of the other areas, and you can help me a little bit on the timeline if i if I don't get it perfectly right, that I thought was interesting was, you know, Vanessa eventually leaves LiveRamp. So for a period of time, you're reporting into the Axiom GC. I mean, I'm curious, like, you know, how does that change the team dynamic?
00:24:06
Speaker
um and yeah I know Vanessa has a particular leadership style. It's one that I really admire. I'm curious, you know how how you how do you manage having a different GC as as your boss? um It's not something that happens, I guess, to folks all that often, maybe because once you're in the GC seat, folks tend to stick around for at least a little while. Yeah.
00:24:26
Speaker
Yeah, so so so um that started, I think, um not that much long after the transaction. and Vanessa left to go join Rippling and obviously see what she's doing there.
00:24:36
Speaker
um But I was working for what was the Axiom GC, now the LiveRamp GC, the LiveRamp parent hold code GC. Axiom was an IPG company. um And he was, you know, Arkansas-based, truly, like,
00:24:57
Speaker
our house, Arkansas attorney, you know, like everyone in Arkansas knew him. He's, you know, good friends with Bill Clinton type of guy. And, um, and he had that type of like Southern drawl the way he talked that people wanted to listen. And just, I think you can pick up things from different leaders, um, that you want to take on and emulate.
00:25:23
Speaker
And then there's things that you learn that you want to do differently. And so I think, I always tell folks like when they when they're moving on or when you know if if your boss leaves and someone else is coming in, it's an opportunity to learn a totally new set of skills from a new leader and also learn like what you may want to do differently if you are given the opportunity to lead. right And so you learn structure, for example. like When I went over to Demandbase, I knew that I wanted the privacy team
00:25:57
Speaker
to be working more closely with the commercial legal team than we had been doing previously at LiveRamp. And that was something that I was really um intentional about. um But it's really just kind of like understanding, okay, this is a very different business that had purchased us. This was a very different company or that the the the executives that have come over for Maxine were now much more involved and their styles were going to be much different. And so how do you navigate that and still um you know get budget and hire and build out a team and get technology.
00:26:33
Speaker
like Some of the technology asks were challenging in the beginning. I really had to show why we needed a specific tool and how important it was or why we needed a new head. like We had done a bunch of work on a ticketing system, for example, on how quickly we pick up um agreements, what our response time is, what our turn time is, how many turns it takes to close a deal.
00:26:57
Speaker
We had built all that out and I used that to be able to say like, hey, we used to be able to pick things up in X amount of days or hours and now it takes Y amount of days or hours because our business is growing.
00:27:09
Speaker
That's impacting... cost time to close. And so i need it I need another person on my team to be able to get back to what I believe is the right ratio of time to close. And so those are some of the ways that you're able to kind of convince someone who may not be as used to that type of thinking initially on how to get something that you're really driving for.
00:27:33
Speaker
When did the opportunity to lead legal at demand base come around for you? And how did that ultimately come together that you were able to convince them to hire you and and jump into jump into the GC role?
00:27:47
Speaker
Yeah. um like I joined Demandbase in September of 2021. And so at that time, I had spent about four and a half years um at LiveRamp, two and a half of which as a subsidiary and two of which as the public standalone company.
00:28:04
Speaker
um And I think yeah the opportunity came about, honestly, because someone who I had supported as a commercial attorney at LiveRamp went on to be at the time, she's no longer here now, but the CRO at the time of Demandbase. And I think that she said, look, i'm like here's this attorney that I worked with a bunch and we navigated partnership should deals. we had We had entered into the TV space during that time and she read some of that.
00:28:35
Speaker
And these were not, going back to what I said way earlier around kind of like following very specific rules, this was the Wild West. Yeah. So we had to be really creative on what we were thinking. And so I think if you can establish yourself as a business first creative attorney who's looking to help the business get the deal done or the job done, then that will pay dividends later on This was years later where, you know, DemandVis was looking for a GC and I know she put a good word in for me because she said, look, this is someone that I had worked with before and I and i um and i think that you would be good here.
00:29:12
Speaker
That's great. um Yeah, i I think, you know, of course there's times where you have to hold a line with sales or product or others, but having like a really friendly relationship with those cross-functional stakeholders, I mean, that um this is it's not only good for the day-to-day, but it's also maybe good for your long-term, right? Some of these folks go on to become CEOs or found their own companies or, yeah.
00:29:40
Speaker
Yeah. I'm curious when you joined, the team was pretty small. You inherited a couple of attorneys, compliance. um How did you evaluate what you thought the company was going to need as it as it scaled? And yeah, let's we can start the conversation there and then maybe talk a little bit more about scaling the org.
00:29:58
Speaker
Yeah. um I think I was ah a couple of things. One is I was really transparent in the interview process around um my vision on what the team would need. And I think part of it is timing. I was fortunate to be joining in September of 2021. Like, as you know, in September early There was like a million IPOs going on. Everyone was, you know, like the market was really firing. And I think the position of Demandix was like, we need to become public ready.
00:30:30
Speaker
um We want to fit the profile of one of these types of companies. And so I was able to come in and say, okay, you're, I think like 650 people or something at the time. How many people do you have in legal?
00:30:41
Speaker
Two? One person in compliance? Well, that's not a public company. That's not what a public company looks like. And so yeah if you want me to come in and lead this team, like i need to have some leeway and some budget and some bandwidth to hire the team that we would need to have in place to be the company that we want to be. And so I was really honest around, here's the things that I think i i'm I'm good at.
00:31:05
Speaker
And here's areas where I would need help. And so privacy is one of them. I said, look, I worked at a company that privacy was core to the business. So I know, i know what it takes I know how important privacy is going to be to this company. And at the time, right before I joined Demandbase, had made two acquisitions, one and one of which was of a data company. And so privacy was even more important for our business now going forward. And so I said, we cannot be this profile of a company without a true privacy leader. So that's going to be my first hire.
00:31:38
Speaker
I also said... I am a really big believer in legal operations because I've seen tangibly how much it impacts the business. Without legal ops, I would not have been able to make the argument around headcount and ticketing and...
00:31:55
Speaker
um now AI, but that wasn't even really a thing then. um ah that It's just core to the success in knowledge management, training, all that stuff starts with legal ops. There's way more than legal ops does.
00:32:08
Speaker
And so those were two things that I said at the outset that we need. um Privacy, the team got it. They understood. Legal ops, I had to convince them. And once... They understood the pitch.
00:32:19
Speaker
They got it. Once you brought in a legal health person, they really got it. um But then I was also able to kind of like right size the org to say, yeah we can't have a compliance team of one. um We need to have more folks than that. And so um i was able to build up and make these hires in a fairly short period of time to right size the team for where we wanted to be as a company.
00:32:42
Speaker
um So, yeah. I guess along with that sort of like scaling of the team, i guess there's almost like a little bit of, i would say sort of scaling of self that maybe you have to do as well as you're stepping into what is like your first full GC role.
Scaling Legal Team at Demandbase
00:32:58
Speaker
How did you think about that and trying to be sort of self-aware and think about how you might need to grow as as a leader um in ah in a new leadership role?
00:33:10
Speaker
Yeah. um I think there's two things that i think about there. One is that You have, again, to be honest with yourself around areas where you don't have as much experience and where you need to grow that experience.
00:33:26
Speaker
And then you have to say, who can help me do that? And so I think a lot about in my career, um this concept of like peer group or mentorship and, um,
00:33:41
Speaker
like mentors are not always like, hey, will you be my mentor? You know, I think that, like I said, even back at the firm, there are folks who I really learned from I feel like I want to get as much work or attach myself to this person as much as possible because I want to sponge up, soak up with their what they're telling me. And so um things like employment,
00:34:02
Speaker
we had an employment attorney at LiveRamp. I never dealt with employee issues before. Now I i run that here at Demandbase. It's something that i think is challenging and interesting. um But I asked a peer group, I joined a peer group and i I joined dinners and conferences and things like that where I could meet people.
00:34:20
Speaker
And my mindset was like, go to these things and meet one more new person, right? Who um you can build a relationship with. And it's not a transactional relationship. It's not,
00:34:32
Speaker
what can you do for me? But it's like a true relationship. And then once you have that core group, you're able to say, has anyone ever seen this before? um i don't know what I'm doing here. Like you have to be honest. I don't, I haven't seen this before. I don't know what to do.
00:34:46
Speaker
Have you seen it? Can you help me through it? um And that's a lot of my kind of like go-to initially before I reach out to outside counsel or someone who I'm, who I'm having to pay for. Um, it's building up this strong network. Like, like you said, many of a few of whom have been on this podcast or other podcasts, right? It's like, these are folks who are super smart, uh, have been, have unique experiences themselves and you stay in touch with them and you say,
00:35:17
Speaker
hey, this is an issue that I'm dealing with. Have you seen this report? like Maybe they say no, but i have a buddy at this other you know place who has. Let me go ping her, ping him. And that's a that's a new relationship.
00:35:30
Speaker
You kind of create your own community over time. ah Yeah. You mentioned you know joining in 2020. the market being in in place, right?
00:35:42
Speaker
Obviously, and we'll see what happens. I don't think anybody knows what happens even with the market when this episode gets released, so what it'll look like. right yeah one But ah the market around like taking companies public, what investors' expectations are, et cetera, have all really shifted since that point in time.
00:36:02
Speaker
What did that mean for for your work, your ability to keep sort of growing the legal org, How did you have to recalibrate maybe some of your own expectations? Yeah, that's a good question. I think that um I was fortunate. I think that not that I could have planned for what was happening in 22 or 23, and certainly not that anyone can plan for what's happening today at all. i haven't even looked at the market today. but um Don't, it doesn't. Yeah. said it doesn't Yeah, it's not going to help or hurt either way.
00:36:40
Speaker
um But I think that there are things that you can do to be a little bit intentional about how you structure a team that could um help you
00:36:53
Speaker
withstand a lot of things that may or may not occur. Right. And so, um, for example, on the commercial side, there's two things that we do here at demand base. One is that, um, we have a strong kind of DP of commercial legal lawyer who, lead who leads that function.
00:37:10
Speaker
Um, underneath him is a contract manager. It's not a lawyer. Um, I'm, I'm a believer in that. I've been a believer in that. I led a team of contracts managers for some time at LiveRamp. um You don't need to be a lawyer um to be doing that work.
00:37:26
Speaker
Another thing is like, okay, that team is small. What can you take off that team's plate, right? And so we do, um we we negotiate all of our NDAs through our CLM's AI ah function.
00:37:39
Speaker
And so I've said this on kind of other talks before, but part of doing that is you, you as the GC or me as the GC has to say, the way we structured it is basically like, there's a few things that we look out for in these and NDAs. And if they are there, it will get kicked to a lawyer. If it's picked up by the AI, it will get kicked to lawyer.
00:37:59
Speaker
If not, it gets auto-signed basically. And so That requires me as the GC to say, I think I'm comfortable with whatever that risk may be, that some things may slip through the cracks and we don't have a quote unquote human in a loop there.
00:38:15
Speaker
And what is the true risk? What's the practical risk? um I think that is outweighed by the fact that we don't have lawyers or contract managers dealing with that work and we have them dealing with the things that are more important. And those things that are more important are...
00:38:28
Speaker
actual client customer work, but also like what the next thing we're going to train our AI tool to do. Is it order forms? Is it MSAs? Whatever it may be. And so it's like, how do you think about the team?
00:38:39
Speaker
The other thing that I do is I kind of, i stretch folks in a way where like there's someone on my team who's super smart and he does some privacy work and some GRC work. He has a background and an interest in both.
00:38:51
Speaker
And so he kind of straddles both of those teams. That has been really successful. I will say it isn't always successful. I had someone doing some legal ops work and some commercial or contract manager work.
00:39:05
Speaker
What ended up happening there was this person who is great, has lasted a year. She left our company because she said, like, I'm really passionate about these legal ops projects. But what ends up happening is I get down the road with them and then I have to stop everything that I'm doing because I have to start working.
00:39:21
Speaker
towards the end of the quarter yeah dealing with all the commercial stuff. And it's too hard for me to balance that. And I'm like, ah kind of thought that might've been the case going in. I wanted her to try it.
00:39:33
Speaker
I get it It in fact didn't work. And now like I'm going to re split those roles again. So you kind of have to like test out these things and see what works and what doesn't.
00:39:45
Speaker
But the theme is you keep the team fairly lean um, to give folks both an opportunity to grow, but also, to hopefully keep your costs down so that when you are in these environments where you have to cut, um, you can insulate your team.
AI in Legal Operations
00:40:05
Speaker
So that's great advice. Yeah. Um, Maybe a last sort of substantive question for you on your time at Demandbase before we get to some fun ones, some closing questions.
00:40:17
Speaker
And I ask this also because, you know, you came to our Spot Dress Summit and spoke on one of the panels. um How you're thinking about sort of the evolution of your team and the evolution of your function as AI becomes more and more what you're doing. I know that you're a very forward thinker on that, as you mentioned, like with contracts managers, as opposed to needing to have an army of commercial lawyers in house.
00:40:41
Speaker
Yeah. um I think that, I don't know. I, I, I hope that I'm a forward thinker on that. I think it's so hard to keep up with everything. And I think that I get, I like probably a lot of other folks in my seat or similar seats get pitched on a new,
00:40:59
Speaker
AI redlining tool tool or AI intake tool or whatever weekly, daily, at whatever it might be. And so I think part of it is um trying to block out the noise a little bit. like you do I heard someone say, i can't remember what it was, I heard another GC say that she takes, but i don't do this now, but I think I should.
00:41:21
Speaker
She takes like I think one call a week on a new vendor that's pitching her to just like see a demo so that she sees what's out there. Like that's an interesting thing to do.
00:41:32
Speaker
What I try to do is, yeah, I think it's really smart. What I try to do is think about um maybe less around kind of like what new tools are out there. Although we do, we have tried a couple, we brought something in house for intake, for example, um that we're testing to show kind of like what type of work do it does a legal What's a GC org do outside of commercial? Because people think a lot about contract metrics and it's like we do so much more than that. We're getting asked all these things from compliance and privacy and risk.
00:42:03
Speaker
um You know, where else can we show that work? So that's one space that I think is interesting. But but a lot of it is How do you give permission and challenge your team to use the tools that perhaps your company already has? So we have, like many companies, a ChatGPT enterprise license.
00:42:22
Speaker
Sure. And so that's key because we don't train on the, it doesn't train on the data we put in. We don't train on the customer data that we, ah that may be part of that. But um so how do you use it, right? Like someone asked you to analyze an agreement because there's a dispute of that agreement.
00:42:40
Speaker
um load the contract into JATCPT and say here and, and write a good prompt, go and take a prompting class. Like I have now taken, Chichilia's GCAI 101 and 201 prompting classes, because I think that's going to be really key. and Awesome.
00:42:57
Speaker
Like yeah that's going to be really key to the success of the function. How do you prompt appropriately? What are the things that I got asked by an auditor to write a memo? Like,
00:43:08
Speaker
okay, here's all the things that I want to go into the memo. And I, and like, maybe I shouldn't say this, but, like, I loaded it through our enterprise license and it gave me the first draft of the memo. Like, why? yeah Because I don't want to spend my time wearing a memo. And I don't, like, and and I think that, like, that's not necessary anymore. So it's less about...
00:43:27
Speaker
Like what new shiny tool can you sign up for? But how do you convey to your team that you want the team to be using these tools and there's ways to use these tools and how are we going to do it? So we built it in through our OKR process.
00:43:45
Speaker
Yeah. I check on in on the team, like, what have you done today? Or what have you done this week around um AI work that could be interesting that you can tell others about? Wow. So it's just like fielding for curiosity and giving permission to um explore different ways to which in which we can use the tools that we're given.
00:44:06
Speaker
I don't know what's going to happen. I mean, I think and the in the long run, there I still get pitched and and I advise actually for a company that's doing like this AI, an AI redlining tool.
00:44:17
Speaker
And I think that it that space is really, really interesting. I don't, I haven't seen something yet that really blows me away where it says I don't need lawyers anymore, you know, or contract managers anymore um at my company.
00:44:33
Speaker
And so, It's funny because I opened up a role for a contracts manager role and one of these companies took my posting, anonymized it, put it on or should anonymize it as my privacy leader would say.
00:44:49
Speaker
put it on LinkedIn and said, it these companies are hiring for contract managers when you could just do, you could use our tool to do the same thing. And it costs way less, like something like that. I'm like making fun of like me and our posting. And I'm like, okay, like I get that, like creative of you. Thank you for not using my company's name, but I just don't know if we're there yet.
00:45:10
Speaker
Yeah, I, ah well, I'm proud of what we're building. I'm proud of the tool that we have and what it does. um It's very much been designed with the idea that there is a lawyer or legal professional in the loop.
00:45:23
Speaker
i And I don't think that we have an expectation. i don't have an expectation that that's going to be changing anytime in the next 12 months, 18 months. Yeah.
00:45:36
Speaker
um Broadly speaking, i think most I think most sort of folks would agree also that you know lawyers who leverage AI, I love that you're asking your teams about how they're using this on like almost a weekly basis or more.
00:45:51
Speaker
Lawyers and legal professionals who leverage a i are going to be massively advantaged in the job market, but it doesn't mean that all the jobs are going to go away either, right? um So, yeah. Yeah.
00:46:03
Speaker
All right. As we come up on, on time, um I've got some closing questions for you. The closing questions that I like to ask all my guests. The first Andrew is if you have a favorite part of your day to day.
00:46:18
Speaker
Yeah. um I think that what I really like about my job, honestly, is that there isn't each day could be very
Day-to-Day Variety and Workplace Preferences
00:46:27
Speaker
different. And so um maybe like the diversity of work is my favorite part of my day-to-day. That's kind of like a cop-out answer, but... um You are a lawyer. It depends. Like, parcing back to firm days, I think that um being in a position where one day you're working not a very strategic partnership. One day you're doing product work. One day ah you're dealing with an employee issue. One day you're dealing with, uh, you know, fundraise, um, like that ah litigation, you know, like being able to, um,
00:47:04
Speaker
um
00:47:07
Speaker
have a day where where your days or have a job where not where your days aren't the same um is really interesting to me. I think that we've been doing a lot of work around... What's also interesting is the things that fall outside of legal. So I think that...
00:47:23
Speaker
um having the opportunity to be viewed as not just a legal leader, but as a leader at the company um is interesting. And so, you know, we're managing through um culture shift and high performance culture. And what does that mean? And how do you set your OKRs to that?
00:47:42
Speaker
And how do you inspire the next line of leaders at your company? like That's not a legal problem, but it's a problem that needs to be addressed for our company to be successful.
00:47:55
Speaker
And so I really enjoy doing, thinking about that type of work. Absolutely. Um, Okay, I think this one's kind of a funny one, and I have no idea what your answer is going to be.
00:48:08
Speaker
Do you have a professional pet peeve? Yeah. um I have kind of like a silly one, and I have more of a real one. I think like the the like sillier one is, and folks might even know this, hate weather talk.
00:48:30
Speaker
And so like a lot of times you get... You get on like a Zoom, particularly like with people who don't work a lot together. And it's like, oh, man, it looks beautiful out there. Yeah, it's 75. Like, how about you? Oh, it's super cool here in Chicago.
00:48:45
Speaker
I hate that. like guy ah Like, it just feels like if we're going to do the small talk, let's small talk something else. I am guilty of that all the time. But um but I think like I tend to go... The flip side of that is when i when I get on calls, I get... My Zoom personality, I think, is a little bit different. like I go straight to the point. And I've been given feedback that like sometimes you have to do the little bit of chit-chat and small talk in the beginning.
00:49:17
Speaker
ah And whether talk is a good way to fill that, just... yeah um I even think it's more real is i I take, I took a lot of pride and I take a lot of pride as when someone asks me to do something and I say, I got this, that I'm going to do it.
00:49:34
Speaker
And so my professional pet peeve is when I'm asking that of others, um, cross-functionally on my team, whatever, uh, is like, I have faith that when you say I got this, I'm going to handle it. You got it.
00:49:47
Speaker
And so, um, it's great when I don't have to follow up, but if I follow up more more than one time, like that is actually, um I'm like, oh, well, maybe you don't got it, right? Like, like if you set the deadline, you say you got it. Like, i i believe that you are going to do that because that's something that I've tried to um live by.
00:50:06
Speaker
Absolutely. um Is there a book that you'd recommend for the audience?
Book Recommendations and Reflections
00:50:11
Speaker
Yeah. um So I was, i saw that you asked that earlier. and I was thinking about it. I, there's a few. They're not.
00:50:18
Speaker
Great. I can't, they're not like tech necessarily. I have one sort of techie book, but. um Two books that I really liked recently. One is um that a lot of folks have read is Anxious Generation run by Jonathan Haidt.
00:50:33
Speaker
um I have three little kids. I have a five and a half year old and I have two and a half year old twins. um And so it's not as much about my children's generation.
00:50:45
Speaker
um It's a lot about like Gen Z, but it's about how devices and the use of devices. It's basically a juxtaposition of how we have vastly under-regulated devices for our kids and over-regulated the real world in the sense that like kids aren't just like walking around, going to town by themselves or being dirty.
00:51:07
Speaker
They're being monitored and tracked. And I think he that he sets this in like a very um like Malcolm Gladwell kind of Ian ah
00:51:19
Speaker
data-driven way to show kind of those juxtapositions and what we can do about it And I just find it really fascinating. And it's something that kind of like young parents of my generation, I think, are talking about. How are we going to do something differently for kids our age? That's one.
00:51:34
Speaker
Another one on a more personal level is this book called trying and H Mart. Um, i don't know. Oh, I haven't read it but I've seen it in the bookstore and I've seen it on friends bookshelves and it gets all sorts of accolades. Yeah. Yeah.
00:51:48
Speaker
So the author is, I'll just make sure i knew her name before this is, uh, Michelle, uh, I think it's Zowner. She happens to be also the lead singer of a band called Japanese breakfast, which is an awesome band. Really great band. I really love that.
00:52:03
Speaker
Um, But she basically writes this book about... um losing her mom to cancer and how she dealt with it and how it kind of structured her childhood, her relationship with her family, how she thinks about her own, ah ah around time and her own passions.
00:52:24
Speaker
um And yeah, it's a book that really resonated with me. I, I lost my mom when I was in my early twenties. think I was saying it earlier, I left school to go take care of her. And so I think that like,
00:52:36
Speaker
um it it's something that has definitely obviously defined my life, but defined the way in which I think about time and how I want to spend my time.
00:52:49
Speaker
And so it's a thread that has played out through my whole, certainly life, but career too, in the sense that like, even going back to that O'Melveny interview, I was asked like,
00:53:03
Speaker
something the ah along the lines of like, how important is this job for you? Like, and I think my answer was like, look, this is a really important job and an opportunity, but I've been through a bunch of other stuff in my life that is actually important. So I want this, but if I don't get it, it's okay type of thing.
00:53:19
Speaker
And so I think it just helps, it helps set your foundation. Um, so that I think is really great book. Um, the last one on a more techie one, is i just finished,
00:53:31
Speaker
Elon Musk by Walter Isaacson. And i am not a like Musk super fan or anything like that. But I do think that I do think that his, this concept of first principles, um,
00:53:46
Speaker
challenging everything, challenging the requirement, asking like, why is this this way? and specifically like who made this this way? And it's not just that the legal department made it this way. It's Andrew in the legal department made it this way.
00:54:00
Speaker
Okay, go talk to Andrew. Why did you say this thing? I think is a really interesting way of thinking and particularly around like the SpaceX and Tesla stuff. all of these things that he is challenging.
00:54:12
Speaker
um It's just like really amazing to see how, what has come from that. So those are three books that I think are ah worth reading. Those are great recommendations. I'll have you back for just more book recommendations. we can do a whole blog post together. but but it Sounds good.
00:54:30
Speaker
ah Who knows if I'll even have to ask this question after the second book recommendation that you gave, but this is my traditional closing question for my guests. And I want to ask it to you too, Andrew.
00:54:43
Speaker
It's if you could look back on your days as a young lawyer, maybe just joining Melviny podcast, Something that you know now that you wish that you'd known back then.
00:54:56
Speaker
Yeah. um i I think it's getting out of comparison. I'll call it comparison culture. And I am still guilty of this today.
00:55:07
Speaker
And I think it's something you're constantly having to work on, which is you you don't know where your career, you can shape, you can shape your career in a lot of ways. Like this is what I'm looking for. I want to be the small team. I want to do do these because I want a big impact. i want to do this and that.
00:55:27
Speaker
But I think that if you spend a lot of time looking around law school or the firm or whatever, and say, this person is more successful for me than me, or this person has got this and I don't have this.
00:55:42
Speaker
Um, it's a lot of noise, honestly. And so I think that if you can like acknowledge it as something maybe to drive you because you're driven, but not spend a lot of your time thinking about how do i look more like this person or get this or compare yourself to that and just focus on what are the things that you really want to get out of your career or work?
00:56:11
Speaker
Um, While still, like I said, like having people to be somewhat of like a North Star, I think that that is a healthier way to go about ah this career and, frankly, life.
00:56:27
Speaker
That's a great sentiment to end on. Andrew, this has been a lot of fun. Thank you so much for joining me for this episode of The Abstract. Yeah, thank you. it'sween It's been great. i really appreciate it. And to all of our listeners, thank you so much for tuning in. and we hope to see you next time.