Flip the Script: Disruptive Strategies in Legal Ops

The intersection of human expertise and artificial intelligence is transforming the legal industry. In this conversation, Martin Bregulla, our Legal Product Manager at Flank, and Jeremy Hopkins, the Director of Legal Operations at Contentsquare, share their experiences and strategies for integrating generative AI into legal workflows. They discuss the challenges and opportunities this technology brings, emphasizing the human element in successful AI adoption. Read on as they flip the script on traditional legal operations and uncover the disruptive strategies that are reshaping the industry.

Martin Bregulla: I’ll start by saying a little bit about Flank and me. I’m a Legal Product Manager at Flank. We bring AI agents that provide 24/7 on demand expert support, to organizations. These AI colleagues integrate into the existing enterprise stack to resolve requests from commercial teams instantly and independently. In this discussion, we’ll cover a range of topics on legal ops and discover some more disruptive ways of thinking about legal ops, and also give some tactical advice on how to put this into practice. Jeremy, why don’t you introduce yourself and let us know a bit about Contentsquare, your journey there, and how you got into legal ops in general?

Jeremy: Sure, I’ll get my disruptive hat on. At the moment I'm Director of Legal Operations at Contentsquare, which is a digital experience analytics platform and global software company. We have close to 2000 employees, a legal and compliance team of 42, and we’re growing very quickly. 

When I joined the company about two years ago, we branded ourselves as the no-PITA team, PITA as in Pain-In-The-Ass, because the expectation of lawyers is that they’re a pain in the backside, that they get in the way of progress.

My journey has been a long and interesting one. It started in the late 1980s, as a practice manager at a barristers’ chambers, which I did for 20 years. Then, in 2012, when we had the Legal Services Act in the UK, and you could have Alternative Legal Service Providers, that sort of broke me out of that environment. I moved on to private practice. I've done in-house consulting, and I've been almost three years now as an in-house legal ops director at Contentsquare. Even from that first day in 1989, a high level summary of my job was dealing with the service delivery element of legal services, managing people, processes, resources, and budgets. I was doing that in 1989, and I'm doing that now. 

But what's really interesting is how that element of legal services has changed, even though the fundamentals of what I'm doing are the same. It used to be that no one’s listening to you, because you’re not a lawyer, whereas now nobody can meaningfully run a strategic legal function without a legal ops element. Sure, I was managing processes on post-its, and I have a bit more sophisticated tools now. But that’s the journey and where it’s taken me. Legal ops feels like the culmination of that journey, maximizing all the professional skills involved in service delivery and using those to exponentially multiply the legal expertise, which is becoming just another ingredient in the mix of services we’re delivering. 

...what's really interesting is how that element of legal services has changed, even though the fundamentals of what I'm doing are the same. It used to be that no one’s listening to you, because you’re not a lawyer, whereas now nobody can meaningfully run a strategic legal function without a legal ops element.

Martin: Very interesting. So you’ve been in legal ops way before it was called legal ops. Do you think that’s still the right term for this department, or does it actually serve the wider business? I know that’s a bit of a leading question. 

Jeremy: I'm always happy to be led up that particular path. First of all, it's great that legal ops has been recognized as a discipline and that I don’t need to explain what it is. That in itself is a sign of how far we’ve come, enabling a lot of careers and capabilities, supercharging the innovation in legal services. To me, it feels as though legal ops has been a foot in the door for business professionals to get into legal practice, but there’s great potential for a wider scope, because of the skills, the background, and the perspective you need to come to legal ops, almost a helicopter view across all areas of business. You can give so much more to the team, so there is further scope for a legal occupational, nevermind what we call them, to be more of a strategic function that connects the legal team across department boundaries. A modern CLO needs to be much more outward facing, have more visibility with execs and the external environment. 

Martin: Are you seeing this change, where legal ops are becoming more of a strategic partner to leadership, happening already, or is this something you wish to see more of? 

Jeremy: I’ve met peers who’ve got innovation and strategy in their title, so I see it happening. Maybe it shouldn’t be an exception, but I guess it’s not for everyone, it doesn’t suit the size and shape of every team. But for me it’s a natural progression, and you might be missing out. I think it gives you more power to make a bigger difference than a legal team working without that function. It enables you to better understand the workings of a business and allows you to help them navigate, spot risk, and build relationships. 

Martin: I absolutely agree. You mentioned that helicopter view of legal ops, and I think with that comes this perspective on tech. The latest evolution in tech is obviously gen AI. Do you see that come up in practice, and what’s your take on the fear of gen AI? 

Jeremy: Generally, with technology, people need to take a leap to trust it. You embed it in processes, it aligns, and people trust it, because it’s almost not there. Gen AI is different. There is a big fear around gen AI, and I’ve lived and breathed that fear. But for me, the biggest fear is that it’s misunderstood in terms of its capabilities and limitations, leading to improper expectations. There’s too much unhelpful dialogue out there, about its capability to magically solve problems if you chuck it at something, whereas it really needs much more thoughtful deployment. So there’s lots of fear, but there needn’t be. The fear comes from misinformation and misalignment of expectations. The best example of that is when you’re deploying a gen AI tool to solve a knowledge problem. Throwing a gen AI tool at an infinite knowledge problem is very different from throwing one at a scenario where you’ve already got established and mature training and education processes, perhaps an intranet, some helplines, and FAQs. So, you might find that if you’ve already got that in good shape, it’s quite an incremental difference, as opposed to chucking it at something where you’re at ground zero and much more can go wrong. That’s where the risk and fear rightly come from, not from the tool itself, but from the misunderstanding and false deployment of it.

There is a big fear around gen AI, and I’ve lived and breathed that fear. But for me, the biggest fear is that it’s misunderstood...

Martin: That makes sense. You just mentioned the connection between risk and fear. What do you tell people that are afraid of the risks, and what’s your take on risk in general? 

Jeremy: I use the term incremental or net risk, because you also have to consider the risk of not using it. If it’s solving a problem that no one was approaching in the first place, and let’s say it has a 90% accuracy rate, you’ve got those 10% risk that you’re chucking at a scenario where nobody was doing anything. So you used to have a much higher risk. For me, it’s about focusing not only on the risk within the tool, but looking at the wider risk context, all of which can be mitigated, if you deploy it with the right people, set the right guidelines, start small and expand, all those things. 

Martin: Yeah, I absolutely agree. I just saw that Zeno from DocPlanner joined, and he put it right in my opinion, that you also have to consider the risk of an overworked legal team. So if you’re deploying an AI to help the team not be overworked, then that also mitigates a risk, rather than creating one. How have you been approaching the opportunities around gen AI at Contentsquare? I know you’ve been piloting with us at Flank since early on this year. What have been your learnings and observations, especially when it comes to the challenges and opportunities that this tech brings?

Jeremy: It’s an interesting case study. We didn’t rehearse this, but what aligned with the rebranding from Legal OS to Flank was that, while we were piloting the tool, it emerged to us that the use case for us was actually bigger in other areas outside of Legal. In our product knowledge team we have vast amounts of technical material that are very well organized on internal conference pages, but the pages are long and very complex. The risk that sits in that is that people won’t read them. They do their best, but they find it hard to read it all and get the right answer. So there was risk sitting in that process. Deploying AI, although it comes with its own risks, is much better, because it’s being fed a load of material that’s already in good shape. The net risk is lower, because people will actually use it. So we’re using it in Legal and Compliance, but we’re starting with a smaller focus on RFP requests. It’s all about identifying your biggest use case, mitigating the risk, and growing and evolving from there. 

Martin: Yeah, that's really interesting. We’ve seen a very organic adoption of our tool by other business functions. When we started, we wanted to remove blockers from commercial teams produced by the legal team, them doing the work and sales teams having to wait on them. But we saw, once we had deployed with legal teams, that other business functions had exactly the same problem. Commercial teams were waiting on other business functions as well. What have been the biggest blockers that you’ve seen when it comes to improving processes and removing bottlenecks for commercial teams? 

Jeremy: I’m pretty lucky to work in a company, where at the moment it’s growing so fast, we can’t afford not to change. Typically lawyers have change management issues. They’re risk averse. But when you’re thrown into an in-house legal environment, as opposed to private practice, you don’t get a choice. The change is imposed upon you, or you get swept away. For me, the biggest block of change is cultural, it’s within lawyers. Even with in-house lawyers, you have this service mentality, where you’re in love with your inbox. Lawyers are from private practice, that’s where every legal DNA comes from. You feed on demand. You want to be wanted. Your happiest days are spent responding to emails. You tell people you want to do the more important strategic work, but you’re too busy. There are things that you need time and space to get control of. Go out and understand processes within your business, build relationships. Those aren’t things you do when your inbox isn’t busy. Those are a key part of your day job, it’s not subordinate to responding to things. It’s absolutely critical. So that’s my disruptive piece. Your inbox will always be full, but you need to realize what your role is, to find the scope and purpose of what you’re doing. It’s not just answering emails, doing what people ask of you and feeling satisfied with that. 

Martin: I agree. Especially in Legal there’s this glorification of being busy. In the end that results in people working really reactively, rather than strategically. What are some of the more unconventional approaches you’ve taken, especially when it comes to prioritizing problems to solve for? 

Jeremy: When I joined the company about two years ago, we branded ourselves as the no-PITA team, PITA as in Pain-In-The-Ass, because the expectation of lawyers is that they’re a pain in the backside, that they get in the way of progress. Our CLO did that, because the company was growing so rapidly. Our idea was that we’ve got to move faster. Our business is at a critical stage of growing, so let’s treat that as our brand. Every time we’re conflicted about a problem, let’s come down on the no-PITA side. Let’s make it happen, build a solution, get stuff done. That was kind of unique and disruptive, and it was great and really powerful at the time, but it’s not forever. The company is more mature now. We need more compliance and risk assessment. We need to change our brand again. The no-PITA brand was to make everything into a Yes, but that’s not actually our job as an in-house legal team. We also have to manage risk. We want to be enabling things, but we also need to be able to control things. So we rebranded our legal, privacy, and security teams as trust teams. Now it’s all about being trusted. The easiest thing for the risk function to do is say No to everything. You need to be trusted to say, We’re not going to do that all the time, we’ll enable what we can and have constructive dialogue about everything else. There’s a nuance shift in branding and how we behave based on where the company is, how we’re trying to react to situations, and how we’re perceived by others. We don’t want to be the department of No. We want to facilitate things, but not be frightened to make the hard calls. 

Martin: That makes sense. With all the experience you’ve got, what are some of the things you wish you’d known sooner rather than later? 

Jeremy: I wish I’d understood the value of what I was doing earlier. I spent so many years battling doubts, frankly wondering what the point of me was. I worked really hard for people to understand the point of me. Only many years later did I realize there was a huge amount of value in what I was doing. Anyone watching this, you have, whatever your title, whether you share the same job title as 50 other people in the same company, your own unique point of view, based on your experience, your background, and the challenges you’ve faced. All these things create a unique perspective that transcends your title, it transcends hierarchy, and it’s really uniquely valuable. It took me so long to realize that, whereas now it’s resounding and clear. It’s not a regret, but if I could turn back the clock with that knowledge, I think it would empower a lot more change in myself, in those around me, and hopefully in the industry. 

This is an adaptation of the abridged transcript. You can catch the full conversation here.

If you want to know more about our AI agents, you can reach out here.