Clio Con Clips 2025 - Ronnie Gurion - E02

0:00Ronnie Gurion:Welcome to ClioCon Clips 2025, recorded live from Boston and proudly sponsored by Clio, the world's leading legal technology company transforming the legal experience for all. I'm your host, Rob Hanna, and over this special Legally Speaking podcast series, we'll be bringing you exclusive conversations with the brilliant minds behind Clio, the innovators, strategists, visionaries driving one of the most transformative companies in legal tech. Across these interviews, we'll explore how Clio is uniting brilliance across teams, technology, and communities worldwide. From AI and data to leadership, culture, and the future of client experience, you'll hear from people shaping what's next for law and redefining what's possible for legal professionals everywhere.

0:46Ronnie Gurion:So whether you're a lawyer, technologist, or leader passionate about innovation, you're in the right place. This ClioCon Clips 2025 is where brilliance meets purpose and the future of law takes shape. Let's get into it.

1:03Ronnie Gurion:Welcome to the Legally Speaking podcast recording live here in Boston for our ClioCon Clips 2025 series sponsored by Clio and I am joined by name, title and organization. Hey, I'm Ronnie Gurion. I'm the Chief Operating Officer of Clio. I'm very excited to be here today. And it's a real pleasure to welcome you back on the show. It's been a tremendously huge year yet again for Clio. Before we dive into that and ClioCon, I'd love to know a fun fact that folks may not know about you here at ClioCon, Ronnie. Let's see. I guess one thing is I have three passports and I'm getting a fourth in the process of.

1:38So I'm a spy in my alter ego. That's just greedy. Well, I got my UK passport, but then when Brexit happened, I figured I have the ability to get an EU one. And so getting that one for more flexibility.

1:52Ronnie Gurion:Good for you. And you definitely get around the world, that's for sure. And you've helped scale Clio into one of the most successful tech platforms in the legal industry. There is no doubt. What's been your biggest focus operationally this year? Good question. I mean, in general, I would just say as we've continued to scale, it's around how do we make sure we stay focused as an organization, that we're aligned on a discrete number of really key initiatives that we put weight behind them. So we are ambitious to try to tackle numerous things, but we don't get spread too thin, and that we do so in as organized and coordinated a manner as possible.

2:29So how do we scale the org? What's the org structure? What's the business cadence? Kind of just how do we really think about that holistically so that we can be as successful as possible?

2:37Ronnie Gurion:Yeah, and I mean, it's been a tremendous story. I mean, I remember sitting down in Austin last year with many Cleons having the interview, and the theme was Amplify Your Impact. And 12 months on, you've absolutely done that as an organization yourselves. I know in Jack's keynote, he talked about the flywheel effect and those inputs. And, I mean, there's been V-Lex, there's been Sharedu. There's been a hell of a lot in a 12-month period. And this year's theme is all about united brilliance. So how do you unite brilliance across global teams to maintain innovation and agility? I mean, you're asking hard questions, Rob.

3:06As usual. When we get the most senior people on who are making these decisions, we want to know. I think as you scale, there's different stages of scale. And what are you optimizing for? What's the focus? I think I joined four years ago. When I first got here, it was about how do we bring in new talent, where we needed to amplify or build out new functions? How do we put those teams in place? How do we put in the right cadence for the business to know how to operate at the next level of scale? I think as you get bigger now, we're probably almost three times, if not more, in terms of number of people.

3:38And with that, as we've expanded, now you have more products, more regions, more business units. You really need to be careful to not let bureaucracy and let fiefdoms kind of creep in. So we spend a lot of time on making sure that we're all really, both culturally, from a metrics and incentivization, and just from objectives. We're aligned on a discrete number of things that show up in annual planning, quarterly, you know, OKRs, MVRs, and then the way that we kind of come together. So there's a lot of intangibles in that, but that ultimately is going to be necessary for us to continue to succeed and not get bogged down.

4:20And I'm very conscious that as we get bigger and even more complex with Sharedu and Vilex, that's top of mind for me and Jack and the team. just how do we structure ourselves to both diversify the business but also not lose that really great culture and coordination and singular focus on everybody really just rowing towards what makes Clio successful as opposed to what makes my business unit or my P &L or this or that. And that's really hard to do. And so far, I think we've nailed it. And we look for that in leaders. We don't tolerate that behavior when we see it. And we kind of coach and guide people towards

4:54Ronnie Gurion:that culture and it really helps us. And that's what I find so inspiring. We've had the pleasure of collaborating with Clio since 2021 and you've experienced exponential growth and exciting acquisitions, first here, there and everywhere for everything in the market, now servicing obviously small to high, but you've never lost that culture. The people, they truly buy into the mission to transform the legal experience of all. And that has to be credit to yourself, Jack and all of the senior team feeding that down because Clion's on the ground here. They really believe in what Clio that I was trying to achieve, and it's just super inspiring.

5:23Ronnie Gurion:And yourself, Ronnie, you've come from huge organizations, super impressive background, Uber, Airbnb, I could go on. And how have those sort of organizations, if at all, helped you manage the hype of growth here at Clio? Well, I think what you see, and at other places that I've worked too, is when you, you have to have the right idea, which is actually not the hard part, and then you have to be urgent, but be patient.

5:53you're not going to see success on day one, but you kind of build and you put enough weight behind something that you give it a real chance to succeed. And then where you see shoots of green early success, it's about doubling down quickly, having that conviction. And we've seen that with our international expansion, with mid-market. We now have over 1 ,500 mid-market firms. That's grown massively over the last few years, several years. And I think with Enterprise, with Sharedu and Vilex, We see that those are great businesses that have really strong foundations, and we're ready to really invest behind those.

6:28And we've had great meetings with a lot of enterprise customers here at ClioCon this year, which is a new kind of audience for us bringing here at ClioCon, and I think that's key. So I think where you see, you don't want to be scattershot, but where you get really choiceful and you see success early, having the confidence and conviction to know you don't have it all figured out, but invest behind it. If you put the right people behind it, things just compound. And you look back after three or four years, you go, oh, my God, we've gone from, you know, a startup idea or a very small team to now a really meaningful part of the business.

6:56And you're seeing that in multiple avenues of the business. And that's really what's needed to, you know, sustain our growth.

7:01Ronnie Gurion:Yeah. And I want to double down on enterprise. Myself, I've been sort of headhunting, recruiting in big law for well over a decade. And I'm very excited about Clio's play. I said to Kurt, actually, the CFO, obviously, the organization, I wasn't surprised when Clio did this because with the mission to transform the legal experience for all, of course you're coming for the whole market. I was excited. But from your perspective, the launch of Clio Enterprise has required a lot of structural changes within the organization. So how did you actually prepare it so well for that shift? Because it seems seamless from the outside looking in.

7:32Well, first of all, I mean, I think it's early days. So the VLX acquisition hasn't officially closed yet. So we've been doing a lot of planning for how we do plan to integrate it, which we will do and with Sharedu already in tow that is a 100 % enterprise focused business they do great in the UK and in Australia they have not focused on the US market to date a part of the acquisition is bringing Sharedu into the US which we you know have announced now as Clio operate and we've got a growing pipeline of interested customers I think that platform is really unique yeah so I would say that's one of my main focuses for the next year is actually to stand up this new Clio Enterprise division that Jack talked about and unveiled in the keynote.

8:18We're putting in the right organizational structure. We're investing a lot behind that, both existing resources, but also a lot of net new resources to really accelerate that push. Because we know that there's a lot of great capabilities that we have that are relevant for the enterprise, but we need to approach it in a different manner, different sales, different CS, different level of product development that is going to be necessary. There are some things that can amplify across both small and midsize law and big law. But we're not being like cavalier or unaware or arrogant to think that what we've done well at this point can just, you know, walk into enterprise.

8:57We really want to listen and understand. So getting that enterprise, I think we've done a good job phase one, but there's a ton more to do. And that's going to be, for me and the rest of the team, one of our main focuses here in the coming couple months and quarters.

9:10Ronnie Gurion:And it's a focus, but I know you're not also neglecting the solos and the mid-size because you've had huge successes. And I know you're doubling down on that. But I do just want to stick with the enterprise for a moment because I found Jack spoke with real conviction in his keynote around. We're not just dipping our toe in. We're coming for this. Absolutely. And so, you know, it's all success. It's all exciting. But, Ronnie, you're in a very high pressure, stressful role. I don't want to sort of suggest five years time because there's so many moving parts in the world we're in. But looking at what you're trying to achieve in enterprise, what's going to be your greatest challenge over the next 12 months?

9:40In enterprise specifically? Yeah. It's twofold. It's getting the right organizational structure in place. So where do we really have dedicated resources focused on enterprise? Which functions make sense to truly 100 % dedicate? Where do we want to have shared resources that kind of span across Clio and then how do we set those up in the right way and how do we get the teams working optimally well together and we're adding a lot of net new heads. So a lot of ramping of hiring the right talent, getting the team ramped up, etc. So that's one. I think the other one is just the, and they go hand in hand, right?

10:12The branding. A lot of people think, like Jack will say sometimes, we did too good of a job branding Clio as the platform for small law. I mean, it was great for the last 17 years. And we faced that when we wanted to go into mid-market. I think we've overcome that now. I think people understand our product is really well suited for mid-market, and it's doing incredibly well there. And it's even a bigger leap now to go and make that pitch to enterprise. Now, I think the benefit is the companies at a stature now that even two, three years ago would have been harder. I think now more and more people see the success and the great traction we've done.

10:49So I think there's a very much eagerness and an openness to exploring it. But they have to learn about Clio. And then we have to prove that out, that we understand how to work with enterprise. It's a different type of customer base and needs. And just that branding and that relationship will take time. And given the cycles, the buying cycles in enterprise are obviously much longer.

11:11Ronnie Gurion:It's a lot longer process. Much longer. Absolutely. You know, it's years rather than months and so forth. Absolutely. One thing I want to talk about is hiring because it's very clear, you know, Clio is hiring humans. We're in this AI world, but there is a real push to get quality talent as you have done for many years through the door. So people that have been inspired by these series of interviews, we've spoken to people across the organization. What do you look for in terms of traits for people who do well within Clio? I mean, you talked about it earlier. you're a great partner of ours and you see firsthand the culture.

11:41It's probably the greatest culture of any of the companies that I've worked at. I'm older. I've worked at a lot of companies than some of our younger clients. But I'm just amazed at the passion, the conviction, the energy, the optimism, the can-do attitude, the collaboration. I mean, those are all kind of buzzwords. But, man, I come home and I just feel like very lucky to work at a culture. And I give a lot of credit to Jack and the early team. It was a great culture already when I got here. And luckily, we've been able to maintain it over the last four years that I've been here. But that precedes, I think that's from the earliest days.

12:15And I think that's from the founders on. So we look for that cultural alignment. And then I always look for people who've, at the leadership level in particular, who operated at scale but really, really want to get their hands dirty. Everybody says they want to get their hands dirty. But sometimes when they come in, you realize they're just delegators. that's not going to work at Clio. We're moving so fast, doing so many things and new things. It takes our senior folks to really get into the guts of the decisions and then set the teams up for success. So, but we have to know with vision, what scale looks like, what is, you know, a hundred million, a billion dollar, you know, business line or product line look like.

12:54And how do we get there? And when we brought in those people, we see them transform a function and elevate it in 30, 60 days time and it can even a function that's already operating well they can supercharge it so that's kind of what i look for and when you walk out of an interview and you go i have to hire that person if you don't feel like you have to hire that person you really should just keep looking

13:14Ronnie Gurion:yeah if you know you know and if you're unsure it's probably not the one and what i i get inspired by all the clearance as well there's a clear growth mindset and jack said this in one of his keynotes as well stop asking what if start asking what is the opportunity what is the opportunity if we win the enterprise game? What is the opportunity? Not what if we fail at this? And I love that whole approach and that whole ethos. And that's been driven. And Ronnie, since you've come in, since we've had the pleasure of working together, I mean, you've been a huge firepower for the success of Clear. How does that feel for you personally in terms of joining the organization and seeing what's been achieved since you've come on board?

13:46Ronnie Gurion:Because hats off to the credit, the work you've put in. Well, thank you for that. I mean, it was a great company when I joined. One of the things I look back on my career on when I think about opportunities is the difference between joining a true leadership company versus even the number two or number three, which is an enviable position to be in. And I've worked at both number ones and also successful companies, but that are two or three. And it is a very different mindset usually because, first of all, most of the value accrues to the leaders across most industries. And then more so than that, besides value, you're on this innovation, growth, leading edge mindset as opposed to a lot of times you get quite focused on competitive, closing the gap type of mindset.

14:31So I looked at Clio was already in a leadership position when I got here. And then it was questions, can we maintain it? Can we extend it? And I think we've done a great job of that, luckily, over the last four years. And yeah, I do take a lot of... So my point is it came into a great company. That was one of the things I screened for when I was deciding if I was going to take on a new opportunity. And joining the leader was one of the criteria that I was excited about. and that has afforded us this opportunity to continue to do that. So, yeah, it's been awesome. And I really credit it to a lot of the team underneath me is some real world-class leaders that have just done great work.

15:05Ronnie Gurion:Yeah, and I say it time and time again, we is greater than me. And my late grandfather, who ran a very successful law firm in his own right in the UK, always used to say to me, laddie, anyone can be successful. It's far harder to stay successful. So I think you coming in and continuing that post has been really, really exciting. And I also talk a lot about COI, the cost of an action and not so much focusing always on the ROI. So for you, Ronnie, in your role, how do you define success beyond financial metrics and what does operating brilliantly mean to you at Clio? I used to give a speech a few times internally on this notion of like this winning mindset and grit, which are interlinked.

15:41And there's a lot of research that shows when you have that mindset, organizations that have that succeed time and time again. You know, why are some sports franchises successful for 40, 50 years and others, no matter who the coach is, who the general manager is, who they draft, they fail. And, you know, there's lots of other examples like that. And so, for me, it's the intangibles around, are we working on the right things? Do we have the right culture? And are we thinking long enough term? We really, we have great financial results, thankfully, but we don't get micro-obsessed. You know, many times in just my four years here, we'll say we're going to sacrifice the plan because there's an opportunity to invest.

16:23And we'll go back to the board and we'll say, here's a business case. You want to make a major investment in an area and here's why. And as long as it's well thought out, you know, maybe we succeed here. Maybe we succeed a little bit lower. But you have we have a track record of generally driving a lot of improvement. Maybe the forecast is off. Maybe it's under. But you know you're moving in the right direction. And you have the right time frame. So are you thinking two, three, four years out and not so obsessed with this month or this quarter? And luckily, we have the track record that our board and our management team has the flexibility and the autonomy to make those decisions.

16:58And that is important. Otherwise, you get very constrained in short-term financial results. And you cannot. It's very limiting. So we want to keep that mindset. Jack always talks about that. And so do I. And to be a true growth company, you have to continually focus on the results, the financial results, but not let it box you in too much.

17:18Ronnie Gurion:And I think Clio always comes back to the North Star, that mission. And I think that helps you with guiding the way you take those decisions and the way that you operate. I mean, it's been a huge, huge four years, 12 months for Clio. I mean, I know I can't get the exact answer out of you because there'll be things you can't share. But what excites you most about Clio's growth trajectory going into 2026? I think it's just the diversification of the business. Mid-market is on fire. Our core SMB business is doing incredibly well. The product innovations that Jack showed that go across both the new initiatives but also the improvements in our legacy platform were more robust and I think high impact than ever before.

17:59So I think we're really going to see how do we keep our eye on the ball, on the core and optimize that. And then, look, this enterprise thing is not going to be easy. It's not going to be short. That's going to take a lot of time for me and the team. But these are the two biggest acquisitions we've ever done. We've not been a really acquisitive company. It's been almost all organic with some small tuck-in kind of point solutions in the past. So this is a new... I've spent a lot of time on the integration personally over the last several months, and that's been great. And I'll continue to be really heavily involved.

18:33so just making sure that the large amount of money that we've deployed for both Sharedu and VLex are going to be well spent and that we realize and put ourselves on this trajectory to, like you said, looking forward three or four years where we're going to be really, really meaningful in the enterprise space and continue to serve the whole spectrum of law firms which is, like you said, very much tied to our mission.

18:59Ronnie Gurion:I'm the first to do it, which is exciting. And there's three letters that I want to ask you, which again, you'll probably be a bit coy in your answer, but it'd be remiss of me not to talk about it given where you sit within Clio, and that's IPO. Is that sort of, tell me what you can in terms of your thoughts or the direction of travel for Clio when it comes to all things IPO. Well, I've been at a number of companies that have gone public and that were public. It's a good milestone. You know, not too many companies have the ability. Can you be a 100-year company without IPO? Sure. There's lots of private companies.

19:35In today's world?

19:36Ronnie Gurion:In today's world? Well, 100 years is a long time. I don't know. Ask me. But I think you can be a 50-year company for sure. I mean, there are... I think it'll... Yeah, I don't think an IPO is a requirement. There's lots of paths to value. Yeah. but I think we look at it as it's built a really strong business that has the internal rigor both in terms of execution predictability and systems that an IPO is an option if and when it makes sense for the business and you know our board and shareholders and employees and if we are it'll be a great milestone it really doesn't it really doesn't change that much I know everybody says that like that's the pat answer but I've been at companies that we went public it was great for like a day those donuts and balloons and things like that and then you show up you're like oh i still gotta do my job you know and it's um in some respects it actually adds some complexity of a significant amount of complexity that's why companies are staying private longer so uh it'll be great if and when that's the right thing for us to do but it's not something that i really spend much time thinking about you know we do need to think about liquidity to investors and to employees and things like that.