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Ep 106: Scaling Legal at Speed – Lessons from Carta, Cockroach Labs, and More
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What does it take to scale a legal team in high-growth environments? In this special bonus episode of The Abstract, we feature insights from five legal leaders who have each helped their organisations scale — and survived the chaos that comes with it.
From building global teams at Carta to laying the legal foundation at early-stage startups, our guests reflect on the personal and professional lessons learned along the way. You’ll hear how legal ops, AI adoption, prioritisation frameworks, and even IKEA furniture assembly play a role in building agile, resilient legal teams. Whether you're the first lawyer in the door or leading a 50-person department, this episode is packed with takeaways for legal professionals navigating scale.
Read detailed summary: https://www.spotdraft.com/podcast/episode-106
Topics
Introduction - 0:00
April Lindauer, GC at Carta, on scaling legal from 200 to 2000 employees post-Series C – 0:35
Adam Becker, Head of Legal Ops at Cockroach Labs, on building connective legal infrastructure and enabling smarter AI adoption – 2:42
David Cowen, Founder of The Cowen Group, on legal ops maturity and leading in the age of AI agents – 4:54
Tommie Tavares-Ferreira, Chief Strategy Officer, Lawtrades, on aligning legal priorities with business impact and enabling cross-functional trust – 8:52
Jordan Hatcher, Co-Founder & CLO/COO, The Grid, on scaling legal internationally and staying grounded through hypergrowth – 14:11
Connect with us:
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
Introduction to Scaling in Legal Ops
00:00:00
Speaker
Hi there. This is Tyler Finn, the host of The Abstract Podcast, and I'm coming to you today with a special bonus episode all about scale.
00:00:11
Speaker
We've talked to a variety of legal leaders over the past few months, general counsels, head of legal operations, other folks in legal about how they've scaled their teams and helped their organizations navigate hyper growth.
00:00:27
Speaker
I hope you enjoy this episode. Let's get started.
Scaling CARTA's Legal Team During COVID
00:00:35
Speaker
First up, we have April Lindauer, general counsel of CARTA, about how she scaled her team through COVID. When you joined, CARTA was about 200 employees. Yes. And today the business is somewhere around 2,000 or so. So you've you've literally helped them 10x, I suppose, over the time that that you've been there. um Take us a little bit on that that journey from 200 to 2,000 and maybe some of the some of the highlights.
00:01:03
Speaker
Yeah, I think some of the highlights were I joined um shortly after their Series C fundraising. So I joined at a time when we were really looking to launch what we called our public markets product. So that product was an employee stock option plan for public companies.
00:01:22
Speaker
ah So we ah had just formed a broker-dealer at that time, and so that was really why I joined Carta. I also joined at a time where, you know, their core business, they are an SEC-registered transfer agent, so it was also to help bolster that compliance program as well. And then also just to help manage and scale all of their legal services. So I joke around and say my job when I started was everything.
00:01:52
Speaker
And it over time, and as we went through various rounds of fundraising, we started hiring for more and more specialists. ah Got it. Whether it was in compliance or legal. But i was really I really joined the company as a generalist at that point in time. So I did everything from commercial contracting to employment to IP, you name it. I was managing that along with a small team of lawyers for about two years.
00:02:22
Speaker
And how big is the whole legal team today? It's like 50 or so? Well, I manage today legal compliance and risk on a global level. So we have close to 50 employees globally.
00:02:35
Speaker
Of those employees, um I believe now that 17 of those employees are lawyers.
Scalability vs Flexibility in Processes
00:02:42
Speaker
Next up, we have Adam Becker, head of legal operations at Cockroach Labs.
00:02:48
Speaker
I sat down with Adam at CLOCK in Las Vegas earlier this year for a conversation around how legal ops can help legal departments scale. How do you think about, um, I don't know if these two things are at odd with each other at odds with each other either, but sort of building process that scales and can scale quickly, but also being able, I mean, 500 people, but Cockroach is a very innovative company. So I'd imagine things have to remain very flexible.
00:03:18
Speaker
yeah Right. yeah How do you think about balancing those two things? and I think it's the same part problem with technology now. It's a question I don't have an answer to. we I went in there building to scale, right? Because we the legal team is now more than doubled in size since I've been there. So that's a scalable thing.
00:03:37
Speaker
Everything the company does is you know scaling. How do we make it happen? and But again, now we've hit this technological innovation where maybe there's better ways than there were a year ago, or in my case, a season ago. Right. Yeah.
00:03:50
Speaker
And I think it's a balance between the two. yeah And quite frankly, it's the same thing I see as something like this. You know, the the technology providers in our world are also having this conversation, yes right?
00:04:01
Speaker
ah Are we native AI? Are we putting it in? Are we integrated? Are we buying something? Like, it's the same thing. We have this amazing product that we built, and now we have this new technology, which we have to build into it. So we're all balancing it in a way.
00:04:14
Speaker
And I don't know if there's a right or wrong answer, but we're we're embracing both. i mean I'm pretty sure I'm allowed to say this cockroach labs has become very AI focused and we made it a corporate goal to be an AI native company.
00:04:26
Speaker
Yeah. So we play with AI a lot. We have an exploratory program and legal. We yeah are using more than I ever thought. Uh, know, I'm very excited here to learn. i actually had perfect my GPT is because right now my GPT is overly helpful too much person in there. But we're building it. We're doing it. And it's it's it's cool. And I don't know where everything's going to go, but it's a balance.
00:04:51
Speaker
We still need stuff to work, but we are very open to what's next.
Role of Legal Ops in Business Scaling
00:04:54
Speaker
I also sat down at Clock in Las Vegas with David Cowan, founder and CEO of the Cowan Group, for a conversation around how helping scale your team can also help you scale your career.
00:05:08
Speaker
and I think this builds on a point that you made earlier, which is... I've observed that it's not just that you have to scale legal alongside the business as it scales, but people increasingly see legal as a very important component of a scaling business or helping the business scale.
00:05:27
Speaker
And I think a lot of folks would chalk some of that up, at least, to the rise of LegalOps. um Do you agree with that? ah How do you think LegalOps helps businesses scale, not just legal teams?
00:05:42
Speaker
a really good question It's a really good question. um you I think like in so like in so many different ways, so we're going to get into a maturity you know we're going to get into a maturity um frame.
00:05:54
Speaker
So A, it depends on the maturity of the GC. B, it depends on the maturity of the individual that they've hired to run legal ops. see it depends on you know the authority and the resources that they're going to give this individual i mean it's like right it gets really complex right so but it does like legal ops moves the needle so it doesn't matter where you start so long as you start kind of thing you know like if you're jen mccarran or you're mary o'connell or you're um or your Lucy Basilian, like if you're one of those people, like you're moving the needle, right? Like they're, but they've got maturity and yeah like they've got a decade of experiential knowledge.
00:06:29
Speaker
yeah If you've got eight years of experience or six years or, i mean, it's kind of like baseball, right? So like if you've played high school, college, AAA, and you've had a lot of at-bats or you've, you know, like you're ready for the pros, you know, and then you're not ready for the pros.
00:06:46
Speaker
Because you're rookie in the pros. Yeah. And then you become Aaron Judge. Right. You know, and it's like, oh. But not everybody becomes Aaron Judge. So, you know, there's an impact of legal ops. But I do find, think, maybe the answer that's most helpful here about the role of legal ops is legal ops is becoming...
00:07:06
Speaker
by by authentic nature, a more interdependent part of the business of law and the business. isn it So we are beginning to see intersections of information governance, data security, security,
00:07:24
Speaker
um the various business units. We need a lot of smart people around the table to understand the potential that AI, Gen AI, the agentic workforce of the future holds for us.
00:07:38
Speaker
There's no one department that's going to own this, you know? And so I think, again, think because legal has so much to gain from this that there'll be a lot of sharing and a lot of learning. So legal ops, legal, legal ops is part of legal.
00:07:54
Speaker
I almost don't think, um I think that all of that is coming together at an accelerated rate. And I don't even know what the agentic world is all about yet. I'm like, I'm just beginning to think about that myself. It's like, you're going to be an agent manager.
00:08:08
Speaker
and Wait, right who's going to be an agent manager? What are talking about? What does that even mean? you know i mean, that's where we're all going to be together a year from now. It's not going to be this overbuilding of technology on the floor.
00:08:21
Speaker
I think it's going to be more process around what are you doing? Do you have agents? what are you doing with your agents? I mean, I'm just leave listening to Reid Hoffman. yeah And I'm like, I'm having a hard time keeping up.
00:08:32
Speaker
And if you haven't read super agency by Reed Hoffman, I'm like, I highly recommend super agency because he talks about how the human in the loop is the key and what and who are we going to be in that leadership role of managing these agents. So,
00:08:50
Speaker
I don't think we're going to be displaced. The last of the conversations that I had in Las Vegas at CLOCK was with Tommy Tavares-Ferrera, Chief Strategy Officer at Law Trades and former Head of Legal Operations at Cedar and Peloton.
Collaboration in Scaling Legal Ops
00:09:06
Speaker
Tommy and I had a conversation around why success in scaling legal operations means bringing your cross-functional stakeholders along with you. least an evolution that I've seen where um it's not just that legal is required to allow the company to scale. yeah It's that these days folks look at legal and say, that's actually a very important partner in helping us scale. And I think legal ops is a big part of that.
00:09:34
Speaker
You've done that before, right? I mean, a company like... Rakuten here in the US, Peloton, which obviously experienced you huge growth and you were there for the IPO, you know, Cedar as well. um Talk to us a little bit about how you've helped not just legal orgs, but like organizations scale through your legal ops work.
00:09:53
Speaker
If I was at Peloton for the IPO, I'd have many more millions of dollars in my best cap. But I came- I'm getting the timeline. I came right after. um So so ah why did i get caught on that minutia? Sorry, what was the actual question? No, no, The question was really like, how have you, being at these organizations where there's been not just a scaling legal team, or not just a scaling legal department, but also a really rapidly scaling business, yeah how have you helped the legal team and the wider organization scale?
00:10:23
Speaker
Oh, that's a great question. Yeah. So the um the beautiful part and position of legal operations, one of the opportunities that we have is when a company is growing. like Cedar is a great example. like Series G, this is a growth company.
00:10:41
Speaker
Not like hyper, hyper growth unmanageable, but certainly on a real growth trajectory like projection. um We can come in and look at what the business is trying to achieve. And and if you know, I would hope that a legal operations person is doing this if they're looking around the landscape of like what the business is trying to achieve, they can figure out where they fit into that.
00:11:01
Speaker
And really, like if you're if you're a good legal leader, and certainly you know Vanessa at Cedar was, like you're going, what are the company's objectives? Where does you know the legal objectives ladder up to that?
00:11:14
Speaker
And then legal operations going, and how do I help us all achieve that? right So what does the company want to achieve? What does the legal department want to do in support of what the company wants to achieve? and And then legal operation goes, and I'll make you all achieve it. Right. So if if the company is like hyper growth and trying to drive revenue and it's like closing deals faster than guess what? guess Guess who's working on CLM stuff? Like, guess who's working with sales up to make sure that you're closing deals?
00:11:41
Speaker
Like, you know, if if you're trying to save costs and maybe you're working with procurement to go, what what are we spending money on it? Where you know, where do we wrap our arms around that? Like, so I think the real opportunities in supporting that rate like big scale is that legal operations generalists really have the know-how to know what levers to pull to support growth.
00:12:05
Speaker
And even if it's happening rapidly, and you like I think that they know where to put themselves in to help to achieve those goals.
00:12:16
Speaker
And to put the fine point on it is what you've just described, that sort of framework. also a framework for prioritization. Yeah. in ah In an environment in which there's probably a lot of different priorities or opinions or. The bottom line is like if everything's a priority, nothing's a priority, right? Like so a lot of my time is spent as a legal apps professional, sort of throwing everything on the whiteboard and then going, what's the matrix here?
00:12:44
Speaker
Like, what is the must get done? What is the nice to have? What's the wishlist? Like, what are we not getting to this year? Because like, everything comes in fast and furious.
00:12:55
Speaker
And it's why I probably like, you know, speak so highly of like doing some sort of intake system. Like, It's really actually very important because it's important to see how much are you getting in sort of one pocket that just is maybe not important.
00:13:09
Speaker
And how do you like how do you actually systematize the things that are coming in that need some sort of like bounce back, need some sort of like, here's the answer to your question. Now, which energy of AI that's going to do a lot of that like first pass, maybe answer the question, because a lot of that doesn't need a legal mind. or a legal operations mind. And we do legal ops leaders are really going to find these opportunities of like where do we strategize where we do spend our time and where we don't spend our time, where our lawyers spend their time, where they don't spend their time.
00:13:39
Speaker
But really, like we can't all be everything all the time. But lawyers feel like they need to. Sometimes they want to, and sometimes they actually have to be. So being able to figure out, like where we can put them, where they don't maybe need to answer a question, where that can be like a self-serve thing, where technology fits in and like actually helps us to get that done. All of that stuff, those are really fun problems and challenges. But if you don't prioritize, you will spin out really fast because there's a lot to do.
Scaling Lessons from StaffBase
00:14:11
Speaker
Finally, I recently sat down with Jordan Hatcher, co-founder, COO, and CLO at The Grid and former first lawyer at StaffBase about how he helped the StaffBase organization grow and scale from 80 employees to more than 800 and set them up for a successful IPO.
00:14:33
Speaker
I don't want us to um pass over your time at StaffBase because I think it's really and think it's really interesting and I think you probably have a lot of lessons to share. um Where was the company at when you joined? That's probably a great place to start.
00:14:47
Speaker
Yeah. So um I interviewed in end of June or July. and then started at the beginning of September and even between that time frame I think they'd added 30 people so I was the 80th employee um they didn't have an office here in Amsterdam and I was lucky enough that ah when they offered me the job and I said look I want to stay that we came up with a solution to stay here in Amsterdam
00:15:18
Speaker
And it ended up working out. We had, I think at one point, 40 people or so in the office here in Amsterdam. Oh, wow. And that's a a whole story in itself. Like basically starting the office here as the only exec at the time.
00:15:32
Speaker
um And yeah, they were just getting started. ah they it was the typical Wild West that most of your most of the listeners will understand.
00:15:46
Speaker
And that, you know, AEs could effectively ah make up their own contracts. There wasn't any of the structures in place. I mean, you don't expect it, though. I didn't go in expecting to have a lot of that as the first legal hiring.
00:16:01
Speaker
And also, you know, when you're at the very early stage of a company, which I also see even more now, the focus is keeping the company alive, right? And it's um closing sales, getting some momentum.
00:16:16
Speaker
You're not running a compliance organization. You're not trying to tick every box, right? you're um Of course, you're trying to do the right thing. But, you know, the structures that you have in place at...
00:16:27
Speaker
You know, a 10 million AR business are different than the ones that you have at a 50 or 100 or about to go public. And in the same way, you know, when you're in that sort of one to 10 range when you start, um when usually they hire their first lawyer unless they're regulated, um it' it's just ah chaos in some ways, right? Yeah.
00:16:49
Speaker
What lessons that you drew from your time there or maybe getting them a little bit away from chaos as they basically 10x'd in size yeah over the course of your tenure?
00:17:02
Speaker
Yeah, so while I was there, they went from, as you mentioned, from 80 people to 800 people. think one of the first things that I did ah in the first two weeks, it was, right, we're opening up a new office in London, do all the incorporation and sort it all out. Yeah.
00:17:21
Speaker
Um, one thing is, at the very beginning, if you're joining one of these smaller outfits as the, the first lawyer, it's a moving train and you kind of have to run up and speed alongside of it and join it. Right. In the sense that, um, you can't just jump in and expect to make a lot of change. Right. So, uh, I didn't want to disrupt the quarter. I kept on with their negotiation processes.
00:17:49
Speaker
um they had a ah contract, uh, at the time that wasn't, um, easy to negotiate in the U S. Um, but we kept at it because it was the one that they had. And then we looked, listened, uh, I really heard from the team about where the pain points were and then tried to create something that was more global to go on forward. Right.
00:18:12
Speaker
Um, At the very beginning, you have to really get stuck in So, you know, when we opened the first, rented the first office, I found that office here in Amsterdam.
00:18:24
Speaker
I ordered the IKEA furniture. ah helped build the IKEA furniture. you know, you kind of have to really dive in and ah into anything almost.
00:18:36
Speaker
um Because again, is a fast moving train, right? ah But at the same time, you can't lose focus of what the core of your job is, right? um It's very easy to get distracted by a lot of other things, and you have to focus on that.
00:18:51
Speaker
Later with growing the team, um especially during the COVID crisis and um the size that we got to and then my own story with ah my son who has special needs. Mm-hmm.
00:19:06
Speaker
ah I really didn't take care of myself and I see that at the after having taken the sabbatical and everything else like I focused a lot on work it was an escape ah for me um but it was also really demanding and I ah should have had better tools to either take care of myself or um to kind of handle the work in the right way so that reducing my own personal stress.
Conclusion and Listener Invitation
00:19:37
Speaker
Thanks so much for listening to this bonus episode with stories from legal leaders about how they scaled their teams and helped their businesses scale. Hope you enjoyed this one and hope to see you next time.