Clio Con Clips 2025 - Jonathan Watson & John Foreman - E04

0:00John Foreman: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.

0:45John Foreman: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.

1:03John Foreman:Welcome to the Legally Speaking podcast, recording live from Boston for our ClioCon Clips 2025, proudly sponsored by Clio. And I'm joined by name, title and organization. Jonathan Watson, the CTO of Clio.

1:16Jonathan Watson:And John Foreman, the Chief Product Officer of Clio. Absolutely. Let's stick with you, John. What's one fun fact people may not know about you here at ClioCon? Well, no one knows anything about me here at ClioCon because I've been at Clio for about six months. Fun fact, I mostly just watch television. My favorite show is Gilmore Girls. Love it. And yourself, Jonathan? My fun fact is I have been a professional gamer, was paid to play games before you could make a living doing that, which is why I do this now. Well, let's stick with you then, Jonathan.

1:49John Foreman:That is a good fun fact because Clio's intelligent legal work platform represents a huge leap forward for the industry. But what was the biggest challenge in actually building it and how did your team overcome it?

2:00Jonathan Watson:Oh, man. I'd say the biggest challenge, frankly, is just coming down to the crisp set of ideas and problems that we want to solve during that time. and then combining the greater VLex and Clio and ShareDo and Draft and Managed and Grow Teams all throughout to build this great platform to build Clio work on it.

2:19John Foreman:Yeah, and it's hugely successful. I just came away buzzing following Jack's keynote. And John, coming to you because you've built product experiences at companies like MailChimp and now obviously at Clio, how do you make AI features simple and intuitive enough for lawyers who may be new to this kind of technology or resistant to using it?

2:36Jonathan Watson:Yeah, I think people have gotten a little confused by ChatGPT. They think, oh, AI is a text box that I talk to and I ask questions about like, I've got this strange mole on my back. Do I have cancer? Right. And the fact is, is AI is super powerful. It can do a lot. And so one of the things it can do is just go ahead and do work for you. You don't have to talk to it. Right. Like, hey, just assemble my bill for me. That would be super. Track my time for me. That'd be super helpful. and so I think people have gotten a bit confused by the dominant interfaces. They're like, oh, let's just take a look at the problems people have that take a lot of their time that maybe they don't want to do and we'll just have AI do that thing.

3:19Jonathan Watson:And you can check it. You can check it if you're scared. Yeah. But it can just do it. Yeah. And so we've just kind of been looking at the list of things, burning it down.

3:26John Foreman:Yeah. And successfully doing that, that's for sure. And then, Jonathan, coming back to you, let's talk about Vincent by Clio, which was announced today by Jack in his keynote. you know, it's going to be used by some of the largest law firms in the world. How do you ensure its AI is accurate and ensure that it's trustworthy enough for legal professionals to use? For sure.

3:45Jonathan Watson:It all starts with data. And the data corpus that the VLACs and Fastcase teams have pulled together is one of the largest in the world, if not the largest at this point in time. And that fact-checking ability, that ability to refine your queries, the ability to bring that in when you're testing your product ideas is at the core of everything the Vincent AI team has been doing. And it only gets better from here as the technology gets better.

4:12John Foreman:Yeah, and it sounds like it's still at the beginning. Even if you look at Clio's journey 17 years on, it's a very, very exciting time. So then flipping back to you, John, this year's theme, we can see it everywhere, is all about uniting brilliance. So how do you unite product design, customer empathy, and technical excellence across the teams in Clio?

4:28Jonathan Watson:Oh, we unite brilliance at Clio mostly by working with Jonathan. He's the key uniter of brilliance at the company. But I mean, if you just stay focused on our customers' problems, it unites these functions, right? So we all have different tools that we bring to the table, right? Jonathan's team, well, they know how to write code, right? We have a design team. They know how to think about the experience of our customers. Like, okay, how is this all going to work together? How is this going to flow together? You know, that's too many button presses, et cetera, right? We all bring different tools to the table, but we unite all of these teams by just thinking, okay, what are the problems you're trying to solve?

5:12Jonathan Watson:What do attorneys spend a lot of time on that they would rather not? How do we streamline those things? And if we keep that in mind, keep that focus, then that unites everyone. And the way we do that, honestly, is really simple. We recruit customers. We give them our products, even if those products are super nascent. And we're like, try it. What do you think? Did it work? Does it suck? And then we get the feedback and we keep going.

5:34John Foreman:Yeah. And I love that, again, because it came out in Jack's keynote, the amount of listening Clio genuinely does and staying exceptionally client-centered. And that's, you know, from my time of seeing Clio's journey since 2021, partnering with the show, it's ever so true. And so, Jonathan, coming back to you with the AI and automation expanding across the platform at a rate of knots, how do you keep security, privacy and speed balanced at a global scale, given the trajectory of Clio's mission to transform the legal experience for all?

6:00Jonathan Watson:Yeah, it's a great question and a real superpower of ours in comparison to the market. It all starts with the platform that we develop, the processes, the people that we've hired, and our core set of principles that start with privacy, security, reliability at their core, which leads us to our industry leading uptime, our security and compliance initiatives that we have. and bringing that in where a lot of people are just jumping those lines. We're still bringing those into the AI world very carefully and thoughtfully. And we do that rapidly by just hiring brilliant people. And they're so excited to solve these problems that they spend all day, every day thinking about how we can go faster and how we can check these boxes and work through these various systems in a programmatic way to empower greater development and greater idea creation that comes out of John and his teams.

6:48John Foreman:Yeah, and I see that in terms of when Clio hires people that genuinely believe in the mission and the impact they can have to transform the legal experience for all. And John, Clio is currently serving over 200 ,000 legal professionals around the world. So how do you listen to customer feedback and actually turn that into product improvements that really go on and make a difference?

7:09Jonathan Watson:Yeah, we organize in such a way that we can take in as much of this feedback as possible, right? So like Jack talked about in his keynote, we serve solos. We serve small firms. We serve mid-sized firms. We now serve enterprise firms. We serve firms around the globe, right? U.S., Canada, the U.K., et cetera, et cetera, et cetera. We have people positioned pointing at each of these groups of customers. And that's not just folks on sales and customer support. Of course, they're focused on our customers. We should have product folks. We have designers. We have engineers who are like, hey, we got engineers, product managers, et cetera, down in Australia talking to folks out in Perth about how do you do accounting in Perth.

7:53Jonathan Watson:And it turns out it's different, right? And so this is how we are able to build for global scale is we just have people paying attention to our customers across the globe, talking to them, making sure we account for their needs. Love that.

8:05John Foreman:Love that. And one thing I also love is Clio for Enterprise, which John was talking on there. Coming back to you, Jonathan, because this is introducing a whole new level of sort of technical capability and complexity. What changes when you start building for the world's largest law firms versus those smaller and sort of small size, midsize firms?

8:22Jonathan Watson:Yeah, I think the biggest thing for us is we're built on the backs of people that have been doing this for a long period of time. With the acquisition of Sharedu and the experience that Ben and the team have, along with the VLex team that's been working in the enterprise space for a long period of time. So we're learning a lot from them as we go. And what we're bringing to that is a lot of just questioning the whys and the whats that become these facts that exist in the enterprise space. You have to do it this way. It must be done and that way. And we're just we're working through that problem as we go.

8:51Jonathan Watson:And we're excited to bring a lot more velocity to the enterprise space where typically the requirements slow things down and the rollout processes are slow. But also know that we've done this and we're working with people that have done this and feel very good and confident about where we're heading.

9:07John Foreman:Yeah, and there's a lot of positive energy and momentum going in that space. And I'm excited to see what happens next. John, I'm coming back to you because the latest Legal Trends Report shows AI can reduce cognitive load by 25%. So how do you design features that make legal work not just faster, but actually more human and fulfilling?

9:24Jonathan Watson:Yeah, it's really interesting. A lot of folks out there, when they think about AI, and when I say a lot of folks, I mean folks in the technology industry, the industry that Jonathan and I work in, what they think about is like, oh, okay, you're doing X job. What I'm going to try to do is build a robot that does all of your job, in particular, the stuff you like. yeah right and that's really not what i think ai is best at right yeah ai is best at coming alongside you and taking away those sort of distractions the toil that makes you burn out what's really funny is like if you look at burnout one of the main drivers of burnout is not like working too much it's actually doing shit that you don't want to do yeah and this is where ai can be really helpful.

10:12Jonathan Watson:And I've seen it in previous places I've worked and I see it in a huge way at Clio, right? Where it's like, okay, you want to reduce cognitive load? Well, think about, okay, I'm trying to serve a client. While I'm serving that client, I got to track my time. I got to make sure I track my expenses, put together bills, et cetera. Oh, by the way, my phone's ringing, email, et cetera, because I've got other folks who I might want to intake. I got to think about them. I got to think about conflict checking. And you just start to do this and your mind is in a million places at once. And so you can't focus on the thing you need to focus on, which is the thing you actually went to school for, etc.

10:45Jonathan Watson:Right. So AI is going to do, it's going to turn down the volume on all those distractions by helping people get that work done. So they can focus on the core responsibility. That's super exciting. Somewhere in my rant, I probably forgot what your question

10:58John Foreman:and it's super clear. And that's ultimately what this can help with, you know, AI removing the mundane, allowing people to practice law the way they wanted to practice law in the first place and get a lot more fulfillment from the role. Okay, Jonathan, coming back to you, because you and John work closely between engineering and product. So what's the key to collaboration and actually driving innovation at SCARE? A great sense of sarcasm is where it's not.

11:19Jonathan Watson:Not at all. So usually, yeah, none of that. We keep it mental, mental conflict. Listen, I love working with John. He's only been here a little bit of time, but it's fun. It's exciting. We challenge each other. We fight. we deliver cool stuff for our customers we work with a bunch of great people across our teams and and we just stay in it and i think that's the real key is you got to keep talking keep working on it and that vision of where the company can go and where you think it should go is is the the big motivating factor i've been at the company eight years now yeah and during that cycle you think you'd get bored or you know kind of have it figured out by now and year eight is completely different than year two for me uh in every way imaginable and i think the next future is going

12:04John Foreman:to be completely different as well. And I love that you talk about sort of, you know, challenge is good, you know, respectfully having debate and challenging because you're only ideating and innovating and trying to bring out the absolute best. And so I like that, that you encourage that within the organization. So John, looking ahead, I know it's difficult because things change in a heartbeat with the AI world, but what excites you most about Clio's product strategy and the intelligent legal work platform and where we're heading next? When you look at a lot of software

12:28Jonathan Watson:out there, most software, they're point solutions, right? A lot of our software that we use does like a thing. Yeah. Right. And what's really interesting then is, is you walk into a place of business and you walk into a law firm and, and you talk to folks working there and you'll see them, you know, someone's going to have a dual monitor set up. God forbid they have three monitors. They got a swivel chair and they're kind of like doing work across tools. Right. Yeah. Now think about that in terms of AI and an AI employer and AI teammate. Yeah. Is an AI teammate able to like work across all these different pieces of software you have right it can be really difficult right because all of a sudden that ai well it's it's got to have access to all the apis right etc now think about clio clio our goal is to help attorneys in every single aspect of their job that means our software helps with all those aspects right everything from marketing with grow through managing a matter and manage through accounting through doing the substantive legal work with work with draft etc so everything you can think of what that means then is if we begin to deploy ai teammates into that space they can operate a swivel chair in the software the same way other folks can they can come alongside the attorneys and so that's what we're looking to do over the coming year is go deeper into like, yeah, you know what?

13:55Jonathan Watson:These things don't exist in silos. If I'm doing intake over and grow, that person who's a prospect, they're going to become a client. All those documents need to pass in, et cetera. The AI can start work immediately, pass it in. So that type of thinking, we're just going to take that further and further and further over the next year. And I think Clio is super well positioned to do some incredible things that other companies really can't. Yeah.

14:17John Foreman:And I only see that. And the energy here is electric. So Jonathan, coming back to you before we look to close with some moments and highlights from ClioCon, as Clio becomes an AI-first organization, how do you ensure that your teams continue to innovate responsibly while keeping that human judgment and ethics at the center of every product decision?

14:37Jonathan Watson:Yeah, I would keep the customer there. I keep the law firms close, talk to them a whole bunch. They're the experts in this sort of stuff. and we're just the technology deliverers and the problem framers. So I think keeping customer feedback, the interactions there is important. It's an ongoing debate that happens constantly at Clio, but ultimately we feel like we align with where law firms are going and where they want to go and where they need to go, then we end up on the right path.

15:04John Foreman:You absolutely do. And before we close then, gents, obviously we're quite early into ClioCon, so what's been a highlight moment for you thus far, John and then Jonathan? I mean, can you say anything besides Jack's keynote? I don't think you can, but we'll see what Jonathan says.

15:18Jonathan Watson:It's a pretty awesome keynote, super meaty, lots of energy. And frankly, I used to live in Boston. I love being here with all the brownstones. So I get to be here for work and listen to exciting keynotes. Awesome. Yourself, Jonathan? Yeah, I'll go one layer deeper into the keynote, which I agree with John, which is amazing in so many ways. But this whole concept of converging into a system of action, I think is the most exciting part and transformative part. of everything that we're going to be doing over the next year to two years. And that's it. Yeah.

15:48John Foreman:And I love that system actually because everything's moving forwards. And so I'm excited to see Clio continue moving forwards. It just leads me to say thank you both so much for joining me here live at the Legally Speaking podcast in Boston for ClioCon 2025. If people want to learn more or get in touch with IV yourselves, where's the place for them to go and do that? Feel free to share any LinkedIn social media handles.

16:06Jonathan Watson:Jonathan at Clio.com. That's probably the easiest way to get a hold of me. he's got a one name email address really quite unfair i'm john.forman at clio.com you can also get me on twitter if you want to it's j-o-h-n the number four m-a-n is the handle you can also reach out to me on linkedin or i don't know that's probably it yeah yeah you you can call my mom and she'll get a message to me like whatever you want to do but anyway that that's that's the

16:35John Foreman:levels people are prepared to go to to go to search for you john listen it's been an absolute pleasure having you both here. Congratulations to you and all on team Cleo on a record year. Very excited to see where the future holds. But for now, from all of us here on the Legally Speaking Podcast, sponsored by Cleo, over and out. Thank you for listening to this week's episode. If you like the content here, why not check out our world leading content and collaboration hub, the Legally Speaking Club, over on Discord. Go to our website, www.legallyspeakingpodcast.com. as a link to join our community there.

17:08John Foreman:Over and out.