Episode 1: Pearls On, Gloves Off with Mary O'Carroll

Jenn McCarron Breaks Down Her Impressive Legal Career

In this episode, Mary O'Carroll is joined by her long-time friend Jenn McCarron, Director of Legal Operations and Technology at Netflix. The pair discuss Jenn’s career trajectory, the growth of legal ops, and the massively successful CLOC event they attended recently.

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Highlights from the conversation

Mary O’Carroll

Hello, everyone and welcome to Pearls On, Gloves Off. I’m your host, Mary O’Carroll. And today I have with me my dear friend, Jennifer McCarron. Jenn is the Director of Legal Operations and Technology at Netflix. She is also a member of the Board of Directors at CLOC, the Corporate Legal Operations Consortium. She is passionate about innovation, delivering value, good user experiences, and not least of all storytelling. So welcome, Jenn.

 

Jenn McCarron 

Thank you, Mary. And it’s funny, you introduced me as Jennifer, because you really call me Jenn. And now everyone calls me Jenn. And it’s a two-N Jenn – Not one. Why be average?

 

Mary O’Carroll

So Jenn, we’ve done a lot of chats together by now via webinar, and people can find those online, and we’ve always had a good time. So I expect you to be a regular guest on the show. But most recently, we also had the opportunity to see each other in person at the annual CLOC Global Institute, which took place in Vegas for the first time in person in three years. And I think both you and I’ve been to every single CLOC Institute since the whole thing started. So how was it for you? How was it to be in person? How did you think it went?

 

Jenn McCarron 

Yes, since 2016, I’ve been in it with you. You put on the first one. And all I did was the app. And then we just sat in the back like “maybe one day we’ll speak at this thing.” So how was it for me this year? I keep saying this full circle, right to be up there on stage, filling your keynote shoes, looking everyone in the eyes, giving, and then and then hearing back from everyone. It was an elevated experience. Every year is elevated, and to now have been more involved in the wider production and interacting like that I was floating the whole time. And I’m still floating processing a week later.

 

Mary O’Carroll

Yeah, so Bellagio told us it was the biggest event they’ve had in three years, the biggest in-person event. And other shows have come back, you know, other shows that have been annually there have come back. But CLOC was probably the only one that came back, not at half the size, but bigger and better that it’s done in the past. And that’s so telling, right, about the community that we have. 

 

Jenn McCarron

It’s so telling of the explosive growth. Number one we have officially exceeded the Bellagio capacity – what a great problem to have and future contract term to look at. But we know that COVID is still happening in phases and has people conservative and holding back, so to know some people still couldn’t come and we were at capacity, and it’s their biggest event. So to me, that means the future is bigger, we’ve exceeded, and next year we’ll potentially have more people and more new members.

 

Mary O’Carroll 

Yeah, well, and the new members thing was really interesting, because I know I had this one session. And this surprised me, we asked everyone who was a first timer to raise their hand. Now in my head, I imagined maybe 25% of the room was gonna raise their hands and I think about 90% – almost the entire room – had raised their hand saying this is their first time at a CLOC event which I mean, that was surprising. It tells us a lot about the growing size and the scope and like the prevalence of the role, right? It’s just emerging and more and more companies around the world.

 

Jenn McCarron

I had this same anecdotal observation. Most people I talked to – probably 90% – were brand new to the field and this was their first conference, which I said “Well way to come in on top and hot because we’re firing on all cylinders on this one.” And then when I think about the membership as we study membership inside CLOC, over 4000 members not all of which are in house, a portion of those are in house, but the predominance are in house. If you think of the bell curve, at least two thirds are brand new to field so this field people are flipping their roles, finding us, finding the roles seeing the job descriptions and going, “Wait, that’s me.” And going to their general counsel’s and chief legal officers and and making the pitch I heard a lot of those stories and what an exciting shift. 

 

Mary O’Carroll

Yeah, I love it. 

 

Jenn McCarron 

So exciting and exciting to see just how it continues to hockey stick is that yeah, you do say in graphs that upward trending up into the right, yeah, right on on membership, and not just for numbers sake, but it’s really behind the numbers is what you’re hinting at – standardizing best practices, collectivization. It means we’re starting to change the in-house legal departments, the ecosystem and law firm partnerships, in more uniform ways.

 

Mary O’Carroll

Well, what I think is really exciting is if you look at the change in the landscape of the legal ecosystem, the way legal services were delivered the the players in the market, the amount of legal technology, investment and emergence and adoption, from 2016, the birth of CLOC, to today, it’s been that same up into the right, you know, hockey stick, as you mentioned, right? It’s with the growth of more people asking for it more demand in the market. And it’s from what we saw at CLOC like it’s, it’s only going to continue. We’re just getting started. There’s so many companies that still haven’t, you know, put a legal ops person in place. And when they do, I mean, even more magic will happen.

 

Jenn McCarron

Yeah. And on the on our startup and vendor side of the ecosystem where you’re hanging out now, there’s more VC funding, that’s also hockey stick up over these last six, seven years, tremendously, tremendously. I remember hearing some staggering statistic. Three years ago, VC funding went from something to three acts for legal tech sector only. And so you see that in the proliferation of startups, the competition between startups solving and maybe the same space like CLM. Well, I’m sure we’ll get to that today. But then there’s still problem spaces that will bring on new innovation and new startups. So there’s, there’s more and more to come there.

 

Mary O’Carroll

There are a lot of problems we still haven’t solved yet in legal. 

 

Jenn McCarron

Mary, what do you think is one we haven’t solved? I mean, CLM is getting it from end to end that it’s on the track. But you know, what are the blank spots?

 

Mary O’Carroll

One big question that I often wonder about is, you know, and then I’ve spoken about why legal tech is so much harder than any other vertical in the enterprise, because it’s still new. And we are very fragmented in the way that lawyers work, right? And IP is so different from litigation, which is so different from contracting. So you have all these disparate systems. And I know for any GC, CLO, or legal ops person who shows up new to this role, then they go, “Oh my God, why do I have to buy 10 systems?” If I were in finance, I’ve got one. If I’m in HR, there’s Workday. Salesforce for sales. There’s one thing for everyone, and for us, there’s isn’t. 

 

Jenn McCarron

Yeah, there’s like, 25. 

 

Mary O’Carroll

You need this, and you need that. You can’t really say you only need one, and this is going to be the one you go with, unless, you know, I think there’s some that are trying to solve that. But a lot of the best-in-breed are still going to be individual solutions.

 

Jenn McCarron

100%. And then where you can’t solve, you go with low-code and orchestration software, right? Doing your own version of whatever connective tissue software and data you need. 

 

Mary O’Carroll 

Or trying to use one software and stretching it beyond what it’s meant to serve as some other parts of your department, which, you know, I recommend doing that if you can, but I think that’s one big question for the 20 years from now: what will the legal tech landscape look like?

 

Jenn McCarron

Oh, there’s going to be a lot of gobbling up. I see it as someone who’s gone through two acquisitions in my career. So yeah, I’ve been at a small dot-com and a startup that got gobbled by bigger companies. There’s gonna be a lot of gobbling and it’s kind of the history and evolution and future. That’s how business works. 

 

Mary O’Carroll 

So one thing I have to bring up, because as you were onstage at CLOC in front of 1000s of people, and then at the Ironclad party, and just dancing in front of everyone, and jumping on stage and grabbing mics, people said to me throughout the week, “Jenn is so confident. I’ve never seen anyone with so much, just, true confidence.” Like, is that true? Are you just extremely confident? Is there any part of you that’s got some insecurity? Do you get nervous about stuff? Tell us.

 

Jenn McCarron

Yeah, you know, I still get nervous before any big thing. That’s the right human physiological response to nerves. It shows that you care and that you’ve practiced and you have so much invested. So I always get that flash, and my heart rate goes up just before I’m about to step out at a presentation at work. Or step out on stage like I did with CLOC, but as soon as I’m out, it’s gone. And then it’s a down roller coaster. And that happened for me at CLOC, so that was really fun. The confidence thing is a really tricky formula. I am a believer of, I just read a book and the book title will come to me so we can reference it later. Behaving my way into confidence versus “just having it naturally.” I’ve never had this never come to me naturally. I remember being a young kid and being really shy. And in kindergarten, the teacher saying, “You have to introduce people to other people.” And I’m like, but that’s awkward and weird. And she’s like, well, it’s on my report card or something. There’s just like, there’s a shyness back there. And as a kid, I was like, “Could my voice ever be powerful enough to be confident?” And then those first years, I would hear my vocals recorded in a song, I’d go through this self hate spiral because nobody wants to hear their own voice – it’s an uncomfortable thing – because it sounds different. And well, I wanted to be a musician; I had to hear my voice. You hear it 6000 times later, you all of a sudden are desensitized. You’re just like, “Oh, that’s my voice.” You get used to yourself. So it’s been a long, slow build. And sometimes when I hear, “You were so confident,” I think, wow. I still struggle with impostor syndrome, especially as a creative person who’s in corporate environments. Everyone seems cool with it now, Mary. But in 2001, they weren’t. In 2005, they weren’t. And I’m in New York City in companies that are a little more conservative. It wasn’t until I started working at California companies that they were a little more like, “Bring it. We like that kind of creativity here.” I mean, think about tech. I found it more over time. But I say that because anyone can build and behave their way into confident moments, micro moments. And there can’t be enough of those. And you’ll have a bank to have macro confidence, and you’ll still get nervous. And especially if you’re a woman in the world, you’ll still get this imposter thing sometimes. And that’s okay. You can behave your way through that.

Mary O’Carroll

I agree. It’s funny you say that because I was also very shy as a child. Painfully shy, and now I’m just off the charts extrovert and can’t shut up. But yeah, I was very, very shy as a child. My sister was very extroverted. And I just couldn’t get a word in around her, and we were only 14 months apart and good friends. So yeah, that’s funny now.

 

Jenn McCarron

So we’re like practiced, trained extroverts that started as introverts in a dream.

 

Mary O’Carroll

I think that I’m naturally off the charts extroverted. I just needed I needed my space, I needed my like to learn who I was and to gain my own independent identity. And then once I kind of, maybe it’s the gaining the confidence of understanding who I am and learning my own voice.

 

Jenn McCarron

That voice is so important in life, the life journey with all of this, in all of us. And that’s power of that and the work that it takes. 

 

Jenn McCarron

Okay, so I’m already jumping ahead. But we might have to discuss – what’s the next party we’re planning together? With Ironclad. We’ll get the passed hors d’oeuvres going. Will that be there? What song are we releasing? Is it a record release party? I mean, that party at CLOC you guys threw for Ironclad at the Barbershop in Las Vegas was so fun.

 

Mary O’Carroll

That party was so fun. I think there was a whole bunch of my old Google gang there. And we commented like it felt like a party from the early Google days. And, you know, I hope that that’s the same sort of energy and culture that we’re bringing at Ironclad. I mean, it is – that party felt awesome. It was so fun. The energy, the community. It was great. 

 

Jenn McCarron

It was really a vibe as soon as I walked in, and there were 100 people queued outside, like it was a nightclub to get in.

 

Mary O’Carroll

Yeah, I felt very badly about the people who had to wait to get in. But it was worth it. It was

worth it. 

 

Jenn McCarron

And I think the feedback note for Ironclad is just like CLOC for Bellagio: we’re exceeding our capacity all around. You guys need a bigger event space. If you’re going to host parties like that? Yeah, get all 500 people in off that waiting list.

 

Mary O’Carroll

Well, it’ll be interesting. Same for CLOC, right? We’ve exceeded the size of the Bellagio, and yet, the amazing thing is it still feels intimate in some ways. I mean, it’s enormous. Like you go into that room where the main stage was, and it felt like everyone kind of took a moment to go, Wow, this room is really big. But you made so many individual connections with either new people or you saw a lot of people you knew from the past or relationships you’ve built online, right through social media and LinkedIn over the last couple of years. 

 

Jenn McCarron

Yeah, I think we need to design for that in the future. 

 

Mary O’Carroll

I don’t we haven’t talked much about Netflix or your job. I mean, I kind of meant to go into that. So curious, like, yeah, how big is your team now?

 

Jenn McCarron

My team is… Well, it takes a second because it changes. I was the first, I’ve been here four year. We’re up to 10, and soon we’ll be at 12.

 

Mary O’Carroll

And how are you organized?

 

Jenn McCarron

This is gonna sound very familiar to you. Because you and I have always tracked my pillars… 

Listen to the full episode to learn Jenn McCarron’s Legal Ops pillars and roadmap.

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