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

Transcript

Legally Speaking Podcast sponsored by Clio (00:00)

Okay, so we are now live perfect, okay, so yeah, and if you can just share between you like that That would be great. Are you ready? Ready to go. Okay. Let me just check. We are still live live live. Yes, we are Okay, I don’t know either Yeah, let’s do this. Okay, right. Yeah Welcome to the legally speaking podcast recording live from Boston for our Cleo con clips 2025 proudly sponsored by Cleo and I’m joined by name title organization

Jonathan Watson, the CTO of Clio. 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. 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? 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. 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?

Yeah, I think people have gotten a little confused by chat GPT. They think, ⁓ 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, AI is super powerful. I 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. 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, 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. And you can check it. You can check it if you’re scared. But it can just do it. And so we’ve just kind of been looking at the list of things, burning it down.

Yeah, and successfully doing that, that’s for sure. 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. 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’s been doing. And it only gets better from here as the technology gets better. 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.

How do you unite product design, customer empathy and technical excellence across the teams in Clio? ⁓ we unite brilliance at Clio mostly by working with Jonathan. He’s the glue. 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 to bring to the table, right? Jonathan’s team.

Well, they know how 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 we’re trying to solve? 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.

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. that’s from my time of seeing Clio’s journey since 2021 partnering with the show. It’s ever so true. 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? Yeah, it’s a great question.

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 up time, 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. Yeah, 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? Yeah, we organized 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?

the Canada, the UK, et cetera, et cetera, et cetera. ⁓ We have people positioned, pointing at each of these groups of customers. that’s not just folks on like sales and customer support. Of course, they’re focused on our customers. We actually have product folks. We have designers. We have engineers who are 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? And it turns out it’s different, right?

we have, 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, love that. And one thing I also love is Clio for Enterprises, which John was talking on there. Coming back to you, Jonathan, because this is introducing a whole new level of sort technical capability and complexity. What changes when you start building the world’s largest law for the world’s largest law firms versus those smaller and sort of small size, midsize firms? 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 ShareDo 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 what’s that become these facts that exist in the enterprise space. You have to do it this way, it must be done ⁓ in that way. And we’re just…

we’re working through that problem as we go. 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. Yeah, and there’s a lot of positive energy and momentum going in that space. I’m excited to see what happens next. John, 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? 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, 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.

And that’s really not what I think AI is best at, right? 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. And this is where AI can be really helpful. 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 gotta track my time. I gotta make sure I track my expenses, put together bills, et cetera. by the way, my phone’s ringing, email, et cetera, because I’ve got other folks who I might want to intake. I gotta think about them. I gotta think about conflict checking. And you just start to do this, 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, et cetera, right? So what 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 their core responsibility. That’s super exciting. Hopefully that answers your question. Somewhere in my rant, I probably forgot what your question was. No, 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 John work closely between engineering and product, so what’s the key to collaboration and actually driving innovation at scale? A great sense of sarcasm. I’ve not got that through this interview. not at all. and usually, none of that. We keep it mental. 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 we just stay in it. And I think that’s the real key is you gotta keep talking, keep working on it. that vision of where the company can go and where you think it should go is the big motivating factor. I’ve been at the company eight years now. And during that cycle, you think you’d get bored or kind of have it figured out by now.

Year eight is completely different than year two for me in every way imaginable. And I think the next future is going to be completely different as well. I love that you talk about sort of, know, challenge is good, 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? Yeah.

What excites me the most is when you look at a lot of software out there, most software, they’re point solutions, right? A lot of our software that we use does like a thing, right? And what’s really interesting then is you walk into a place of business, you walk into a law firm and you talk to folks working there and you’ll see them, know, someone’s gonna 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? Now, think about that in terms of AI and an AI employer and AI teammate. Is an AI teammate able to 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 gotta have access to all the APIs, right, et cetera. 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? 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, and I only see that and the energy here is electric. So Jonathan, coming back to you before we look to close with some sort of moments and highlights from ClioCon, you know, 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? 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.

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. You absolutely do. 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?

What has been a highlight moment? mean, can you say anything besides Jack’s keynote? I don’t think you can, but we’ll see what Jonathan says. 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 brownstone, so I get to be here for work and listen to exciting keynots. Awesome. Awesome. Yourself, Jonathan? Yeah, I’ll go one layer deeper into the keynote, which I agree with John, was just 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. And I love that system actually, because everything’s moving forwards. And so I’m excited to see Clio continue moving forward. 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 and get in touch with either of yourselves, why is the place for them to go and do that? Feel free to share any LinkedIn social media handles. 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.

You can call my mom and she’ll get a message to me, like whatever you want to do. Anyway. That’s the levels people are prepared to go to to get in touch with you, John. Listen, it’s been an absolute pleasure having you both here. Congratulations to you and all on Team Clio on another record year. Very excited to see where the future holds. But for now, from all of us here on the Leaguer’s Team podcast sponsored by Clio, over and out.