Filevine is an AI-native legal operations platform that unifies case data, documents, workflows, and teams into a single source of truth, empowering legal professionals with intelligent, context-aware insights. Powered by its Legal Operating Intelligence System (LOIS), Filevine helps law firms, enterprises, and government agencies automate work, verify facts, streamline legal processes, and drive better outcomes through agentic AI.
In this episode, we speak with Keegan Chapman, the Chief Growth Officer of Filevine, a legal technology company. The discussion centers around Filevine’s transition from a case management platform to a comprehensive legal AI platform. Keegan explains how Filevine integrates AI into every aspect of legal workflows, emphasizing the importance of context and data to provide better outcomes for legal professionals. The conversation highlights the challenges and opportunities of using AI in the legal industry, focusing on trust, reliability, and the orchestration of AI to enhance efficiency and decision-making. Keegan also shares insights into Filevine’s strategy for serving a diverse range of clients, from small firms to large government agencies, and the importance of security and customization in their platform.
Watch the podcast here:
Listen to audio only here:
Learn more about Filevine.
Interested in appearing on the SourceForge Podcast? Contact us here.
Show Notes
Takeaways
- Filevine evolved from case management software into a full legal AI platform.
- Legal AI is most valuable when integrated directly into daily workflows.
- A legal operating intelligence system combines data, context, and AI.
- AI should enhance legal professionals rather than replace them.
- Context-rich AI produces stronger outcomes than document-only tools.
- Trust in legal AI requires source citations and human oversight.
- Generic AI tools can create serious legal risks through hallucinations.
- Security and zero-retention policies are essential for sensitive legal data.
- Litigators benefit from AI-assisted preparation, coaching, and case strategy.
- Filevine focuses on solving complex legal workflows rather than isolated tasks.
- Customizable platforms scale better across firms, enterprises, and government agencies.
- AI revenue growth reflects growing demand for outcome-driven legal technology.
- The quality of AI results depends on the quality of available data.
- The future of legal AI is proactive assistance rather than reactive support.
- Organizations that embrace AI effectively will gain a significant competitive advantage.
Chapters
00:01 – AI’s impact on the legal industry
01:35 – Filevine’s evolution from case management to AI
04:04 – What a legal operating intelligence system means
06:28 – Rebuilding the platform around AI workflows
08:16 – Why legal AI needs full context and connected data
11:15 – Trust, hallucinations, and legal AI reliability
16:59 – Human oversight and validating AI-generated work
17:59 – AI orchestration and legal workflow automation
21:53 – Solving challenges for litigators with AI
24:14 – Serving firms, enterprises, and government agencies
28:21 – Rewriting infrastructure and building for scale
30:23 – AI products surpass traditional software revenue
33:14 – Why AI adoption is becoming unavoidable
34:35 – The future of proactive legal AI assistants
39:57 – Leadership lessons and building through rapid change
Transcript
Beau Hamilton (00:01.422)
Hello, everyone, and welcome to the SourceForge Podcast. I’m your host, Beau Hamilton. Now every industry has a moment where the technology stops being nice to have and starts reshaping how the work actually gets done for the legal industry. That moment is happening right now. company called Filevine has been building legal technology for over a decade. They started as a case management platform. And more recently, they’ve been making a pretty aggressive push into AI unveiling something called the legal operating intelligence system at their annual conference last fall.
And the business results have been pretty hard to ignore, I would say a $400 million raise at a $3 billion valuation, and AI products that actually now generate more revenue than the traditional software platform. So whether you think that’s a sign of where all of this legal tech is headed, or just one company’s bet, it’s definitely worth paying attention to. Now our guest today is Keegan Chapman file vines chief growth officer, she got her start at Groupon during the pre IPO days, eventually ran her own go to market consulting practice and actually came to file vine first as a client before joining full time. So she’s really the person figuring out how you sell AI into a profession that’s built entirely around managing risk. So I’ve got a bunch of questions to ask her everything from, you know, what this this legal operating intelligence thing actually means in practice to how you get lawyers to trust AI when the stakes are so darn high. So a lot of questions asker. I want to get right into it. Keegan, welcome to the podcast. Glad you could join us.
Keegan Chapman (01:29.934)
Thank you so much for having me. I’m excited to chat more about this and just what we’ve been seeing in the industry.
Beau Hamilton (01:35.276)
Absolutely. let’s, let’s start at the top for anyone tuning in who hasn’t really maybe crossed paths with Filevine. How would you describe the company today? And maybe you can talk about, you know, how was the company focus? How was their focus involved as this legal tech has shifted towards AI?
Keegan Chapman (01:53.304)
Yeah, absolutely. So Filevine’s been around a while. Really, as you mentioned before, we started as a core infrastructure because over a decade ago, that’s what the industry was looking for, right? A great place to house all of their information in one singular source to help their law firm or legal practice work more efficiently or work together. That really got emphasized through the pandemic as well when everyone needed one place to go for information.
As most will know over the last few years here, it’s not about just having insights and information. It’s about being able to have the right outcomes and help your teams work faster or work smarter or be able to see details that maybe a human who’s burnt out or has too much work could miss, right? So what we have done is made a drastic shift over the last couple of years into being a full legal AI platform.
No one will ever see Filevine without some type of AI throughout the workflow. But what we’ve done is we have leveraged our history, our context, our ontology to help surface those insights that ultimately become outcomes for those legal professionals. So maybe that’s drafting a document. Maybe that’s moving a case forward. Maybe that is bringing everyone together to review an NDA together. So what we’re doing is making sure that we’re taking all the context we have, which is really different than what you’re hearing in the industry where often people are just uploading a document and looking for a summary. And we’re actually saying, how do we help leverage AI or how do we leverage AI to give that lawyer the outcome that they’re looking for?
Beau Hamilton (03:35.276)
OK, that’s really exciting. It’s lot of it’s like automating some of the everyday workflows. But then I imagine also taking action on users behalf in some cases where it makes sense. Right. And obviously doing that carefully and in a manner that the like a lawyer professional can actually trust and validate. One thing I’ve noticed in this space, of course, is every software company is really is is pivoting towards AI and incorporating a lot of features and calling themselves an AI company and maybe even coming out with their own sort of operating system of sorts. It’s becoming one of those phrases that can mean everything or nothing depending on who’s saying it. So maybe you could talk about what does AI operating system actually mean for Filevine? And is it more than just adding more features?
Keegan Chapman (04:26.657)
Yeah. That’s a really good question, So we sat down around a table a couple of years ago and said, how are we going to approach this in what we think is the right way? How can we make sure that we’re helping and serving the client base that we’ve been serving for so many years now in a way that they’re going to expect as this AI era evolves? And I think everyone first started with, let’s put AI somewhere and see how people are adopting it, where it’s helping, where it’s hurting.
Having a bunch of point solutions is one of the original value props that we were trying to destroy with Filevine originally saying, hey, you can bring everything into one place. You don’t have to pay 25 vendors. You work in one intelligent place together. So as we started to think about the core differentiators of how Filevine is going to market as an AI company, we realized we have a legal operating intelligence system. It’s not just legal AI. It’s not just an operating system.
We’re taking both the data and ontology plus layering in AI at the right points in time to help actually those firms or those legal professionals operate more strongly. instead of saying over here, we have a drafting AI, over here we have a scheduling AI, over here we have a review AI. We said, why don’t we input AI into each step of the flow for any legal professional using it so that they can still be the star?
We want to make sure that the humans are in the loop doing the right work, but that they are leveraging AI in a way that will actually help them move faster, get better insights, all within the place they’re already working.
Beau Hamilton (06:09.358)
Okay, I love that philosophy. Yeah, because you’re not just like sprinkling the features into your, you know, the software platform you’ve had for the last decade or so it’s like, you’re actually sort of re thinking it and rewriting it from from the ground up around this a lot of these AI, you know frameworks, right.
Keegan Chapman (06:28.13)
We’ve actually completely been rewriting our code bow. So like I get, I get pretty excited about this because it’s one thing to say, I want to come into Filevine and I want to put my tasks in, or I want to upload this document, or I want to make sure my email is connected in, or I want to use the API to pull in some data from this court software or whatever it might be. That’s, that’s really cool and good, but it’s still all in this place where a human needs to review it, update it, manually put everything in.
Beau Hamilton (06:31.617)
wow.
Keegan Chapman (06:56.066)
We’ve now leveraged AI on both sides where it’s like, how can we make sure that data flows in more easily and more automated? And then how do you leverage that data? It literally sits on top of the platform so that you’re not weaving through pages and pages of intake. And instead, you’re actually looking at the case in an overview in a proactive manner versus saying, I need to upload this document and then go find this thing. It should already know.
Beau Hamilton (07:18.37)
Right. Yeah, that’s, that’s, that’s, that’s great. It’s, makes me, just think of, of where things are going. mean, obviously we, we, we know that people are, are focusing companies are focusing in on AI and incorporating a lot of features and actually, a lot of them, like I was saying earlier, have been AI, like they’re an AI native company now, you know, they, they, throw it into their, like that is, they, they lead with the fact that they are an AI company. but I actually haven’t heard a lot of companies.
Keegan Chapman (07:37.368)
Mm-hmm.
Beau Hamilton (07:47.83)
like talk about the operating system side of things. And that kind of frames it in a new position of, just sort of where things are going. My mind, my, my class example as a X smartphone reviewer, thinking about where things are going on that front. It’s like the next big shift I think is going to be this AI operating system where our phones are, you know, we have like one sort of chat bot that we connect that connects to all of our favorite apps. And it’s all integrated through one sort of interface.
Keegan Chapman (07:50.178)
Mm-hmm.
Beau Hamilton (08:16.75)
And that’s, it sounds like the system you guys are kind of moving towards with the legal profession and industry. And so without getting too redundant with some of the points you mentioned, I’m curious, like, is there a particular problem in the market that led Filevine to build this operating system in the first place?
Keegan Chapman (08:35.07)
Yeah, so I think I’ve even experienced this as a consumer and I always try and look at what’s my experience sounds like similar to when you were reviewing smartphones or something else in your life. AI is coming in and affecting people’s day to day from every angle, right? We’re not selling something that only fits in legal, right? Or only fits in healthcare or whatever it might be. And so people are expecting a certain kind of experience, right? If they’ve tested chat GPT or they’ve tested Claude in their…
Beau Hamilton (08:46.637)
Mm-hmm.
Keegan Chapman (09:04.46)
life or they’re on their Google phone and they’re using Gemini. And they’re starting to say, wait, wait, AI could be really helpful for me with the right information, right? And every person has experienced where they didn’t give enough information to the AI, right? They said the question wrong, or they didn’t upload the document they wanted to reference, or they didn’t have the right language that they used and it connected it to the wrong use of a word, right?
Beau Hamilton (09:08.162)
Yep.
Beau Hamilton (09:19.086)
Hmm.
Keegan Chapman (09:32.096)
And so the way we think about it is how can we eliminate those pieces and actually provide the full picture to the person using it? So let’s say you are using even another native legal AI kind of bolt on tool that probably felt really easy to implement with your team, but you still need to go find the documents you need. Hope you can download the emails that it was referencing. Maybe you remembered to pull the text messages out of your phone. And then you also wanted to make sure it’s linked to.
some kind of case law that you found across a different application. Well, you miss one of those pieces, and it could be the difference between winning and losing a case, right, or winning or losing an argument. So what we’ve tried to do is say, OK, we don’t want you to have to think that hard every time you want to leverage AI for something. Let’s create a place, whether that’s through API connections or leveraging the core Filevine infrastructure, to pull everything that could possibly be related to that moment so that when you go ask a question,
Beau Hamilton (10:09.88)
Totally.
Keegan Chapman (10:31.68)
it’s not missing that client portal message from that client in the middle of the night when they were freaking out that they forgot to send you an image from whatever it was they were talking about. And so I think that’s the real difference in the power. Is it a heavier lift to think about all of the things going in upfront? Sure. But when you think about it, if it’s all there already, every time your staff uses it and you’ve created the right AI policies to have the right data there, they aren’t coming and saying,
Beau Hamilton (10:41.56)
Yeah.
Keegan Chapman (10:58.7)
I’m writing this document in a vacuum with the three documents I thought of today. They’re saying I’m writing an entire outline or in some cases like a demand letter and I have every single piece of the puzzle there to make sure that it is actually representing the right situation.
Beau Hamilton (11:15.81)
Well, so I think the next natural follow up I have after that wonderful explanation of the platform is something that I think probably a lot of legal lawyers are listening to and wondering themselves right now is the trust question. Because a marketing team can experiment with AI, let’s say, and the stakes are pretty low. But if a lawyer files something based on something that’s bad source data, there’s
bad output and then the stakes are completely different. legal, how would you decide, how do you design AI that lawyers can actually rely on and trust?
Keegan Chapman (11:54.026)
it’s such a good question. So I was sitting at dinner with an amazing attorney. We did a really cool retreat where we brought together attorneys from across the US and just got their input on kind of where they’re using AI, where they’re trusting AI, areas where they wish they could apply AI, but they haven’t quite figured it out. And I’m sitting at dinner with this attorney and she says to me, my gosh, you won’t believe what this associate put across my plate the other day. And I, you know, as somebody that’s really busy and wants to keep running,
I looked at it quickly and was like, okay, good, has the site, the sources has the case data I need. I’m going to send this off. And then she had a moment because she’s been practicing law for 20 years. And she said, that case citation looks weird. Something’s off about that. And she went to go check where all that information was coming from. And it was made up. They had put it into some generalized tool that was not
legal specific that didn’t have the guardrails that we believe should be in place. And they had to go back to that associate and said, like, where’d you get this information? Well, a lot of these younger attorneys and associates have been using AI from the day they started at a law firm. They trust it so much more than those senior managing partners, attorneys who have had to sometimes look through books to cite things, right? And so I tell that because it was so, so
clear of a story where it can go wrong. And so that kind of emphasizes where I think it can go right, which and how we do it is we have source cited, data cited information in everything we do. So let’s say we go in and we ask Lois and we say, Lois, pull out all of these scenarios in this document. There will be a source cited linked place and highlighted spot directly in that document where you can go read it instead of just assuming that it worked.
Internally, we can also have them choose, I only want to use my information in my one case. I want to use information from all my cases across my Filevine that I have access to. So we have permissioning in place as well to make sure, Bo, you couldn’t see things you’re not working on or I couldn’t see things I’m not working on. And then we have options to go to the greater sources. Maybe it’s a case citation or case law.
Keegan Chapman (14:19.15)
application or going to Google to see different information that might be there, but it’s going to tell you where it found it so that you’re not going back and wondering if it’s real or not. So I think that’s part of it. But the last thing is just making sure that these legal professionals have some kind of AI policy, right? I mean, that’s in any industry and making sure that their folks know what to use and if it has the right security clearance. So the last advice I would give, which is
really for anyone working on anything sensitive. And given I work on things before they are ever live in the market, I need an AI software that has a zero retention policy. So everyone should be reading their agreements and making sure that nothing is going and training their model. Next thing we know, Bo, we think of some amazing thing in the market, and I talk about it into my AI platform. And next thing you know, it’s feeding the go-to-market strategies for anyone else in the market.
Beau Hamilton (14:57.09)
Yeah.
Beau Hamilton (15:14.178)
Yeah. Yeah. Cause I mean, lot of the, you know, chat discussions you have with like, let’s say chat GPT. mean, they’re at least in the early days, those were being leaked out. They were on an open, you know, people can, can look for the URL and get access to what people were talking about. And, so it’s, it’s a very, you know, serious issue when you, when you’re working from a company side of things with proprietary confidential information. but then the,
I mean, just some of the use cases, the horror stories with AI, lawyers using AI and citing fabricated cases. mean, I remember all those headlines. I think we all, a lot of us knew that would happen eventually. There would always be examples. But seeing it again and again from a lot of these professionals that you think would have the knowledge to not.
go down that path. But it’s just easy for everyone to do. we already, find myself outsourcing a lot of my workflow and critical thinking skills to AI. It’s kind of like, on one hand, it’s useful, but on the other hand, it makes me wonder. I don’t want to rely on it too much. There’s like the balance. But I think what you were saying with having the platform lowest to have, bring forward, review the context and bring forward a lot of the options for
like the professionals using it, I think ultimately it helps them be the decision maker. And again, it’s just a good reminder to always just review, review, review. Don’t take some of the outputs as the end all be all, this is the word of God type of thing. So.
Keegan Chapman (16:59.374)
It’s easy to do that too, but with AI, especially like some of our AI, I was interviewing a different customer and they were saying they had to compare one demand letter to the AI wrote to the one they wrote because it sounded so similar to them in the way we built it. And she was like, this is a slippery slope, right? Because if it sounds just as good as me, your mind starts to trust it almost too much, right? Because we’re all humans. We’re trying to think, how can we get more done faster? You know, even when you’re in the billable hour,
Beau Hamilton (17:12.743)
huh.
Keegan Chapman (17:28.504)
There’s a lot of admin work that if it could be simplified, you could spend a lot more time with your client or working on your case strategy. And so the two areas where we’ve seen humans almost want to trust the AI, but like it’s really important that they’re thinking about how are they elevating themselves as the expert and leveraging that data is kind of in those case law situations, in those drafting situations, in those contract review situations and making sure that they are.
validating what’s happening, even when it sounds just like them.
Beau Hamilton (17:59.178)
Yeah, it’s getting better and better. scary. So, okay, we covered the reliability side, I think. But one of the other things that stood out to me when researching the platform is just that it’s not a tool you ask a basic question and get an answer from. It’s deciding, like you were saying, what kind of task it’s looking at and routing it to the right place. It’s a lot more complex than just combing through
you know, company documentation and pulling up various policies and whatnot. Like we can do a lot of that, but it’s also kind of taking action on your behalf and giving you all these kind of scenarios based on what it is you’re trying to unravel. So how important is that orchestration layer to making AI useful in the legal world?
Keegan Chapman (18:50.7)
Yeah, it’s a great question. I think a lot of people approach AI for the first time and they think, what’s this one thing it can do for me? And I think that’s where a lot of AI companies are. They provide that one point solution, that one outcome that someone’s going to look for. At Filevine, we kind of have this motto that we’re going to actually build the really hard things that no one wants to build and not always the easy things. And one of the areas where we’ve done that, and I think it illustrates this quite
Beau Hamilton (18:58.396)
Mm-hmm.
Keegan Chapman (19:20.558)
quite well is we’ve really focused on how can we serve the litigator, not just the transactional attorney. We can obviously help any type of attorney in any type of space, but to take the litigator who it’s so often such a human component on how they are going to go about that case, how are they going to win, how they’re going to head to trial, what they’re doing in that deposition, those are much harder problems to solve with AI. And so we took that
hard flow that’s very human integrated and said, okay, how can we make sure that we’re not only drafting just one motion or discovery questions or deposition problem? Like how can we pull everything together so that AI is that kind of right hand riding along with you in everything you’re doing, either proactively or reactively? So it’s not, so the way we kind of think about it is like Lois is not just searching and saying, here’s a document, right? Or
I’ll draft this one thing. We’re trying, the way we’ve built Lois is that it thinks alongside of you. So it might pull together deadlines so that you know exactly when all these things are due. It may surface certain documents at certain points in time because it knows you’re in that phase of the case. It may help you build your strategy, right? Because it has all of the context from everything that has come into one place. It may schedule a task for your paralegal to go review something because you
flagged it as you were reviewing that case strategy. We have AI in deposition tools that fit with Inside Lois. So it’s sitting alongside of you and surfacing inconsistencies, risks, ways that the deposition is going against the documents that you’ve already stored and reviewed to prepare for that. what we’re trying to do is say, okay, we understand you are the expert. You are so good at what you do, but imagine if there was someone there with you.
making sure that you didn’t have happy years, which anyone in sales or marketing or any kind of position knows that we can hear what we want to hear. And that you’re getting the right things at the right time so that when you are in that moment, which often is a once in a lifetime moment to find that answer you need, it’s right there with you and you can be successful. So that orchestration layer is taking it so much farther from that one moment in time and instead tying AI through
Keegan Chapman (21:44.958)
every second, every moment, whether you’re on the road, whether you’re in a deposition room, whether you’re in a courtroom and pulling everything together.
Beau Hamilton (21:53.176)
That’s a great explanation. And it just goes to, it goes to show the, how, how many different problems you guys are focused on, on, and areas you’re working on helping, in regards to the different task, professionals are working on there. you mentioned the it’s, you’re focusing a lot on the litigator side of things. is that kind of the, where you’re noticing legal teams feel a lot of the, the, the most pain right now? Is that kind of the main, the main priority?
Keegan Chapman (22:21.688)
think there’s less options for them today, to be honest. Like it’s a harder thing to solve, right? Because there’s a lot of human thinking involved. I mean, one area I was thinking about, mean, people watch Suits, I’m sure. Have you seen the show,
Beau Hamilton (22:34.646)
Mm-hmm. I have, started it. It’s, it’s, got to catch up and watch it all the way through, but yeah. True.
Keegan Chapman (22:39.766)
Yeah, well, now with legal dramas, there’s so many out there, right? You can take any legal drama that you maybe watch. often, and this was just an example, I was talking to this great litigator who’s been using the depositions portion of our lowest software. And he said he will send in a more junior attorney, right? Which happens, right? We have to divide the work, especially on these massive cases. It’s not like, Bo, you are going to handle every single thing.
you would burn out in a minute with how long some of these goes, how in depth some of these are, how many thousands of documents are being reviewed, how many depositions are happening. And he was like, it’s amazing. I can prep using Lois with my more junior attorney. I can prepare the questions. I can prepare what to look out for. The AI is then running and essentially coaching my
junior attorney while in the room so I don’t actually have to sit there and then he can play back the clips, give feedback to that attorney and make them better moving forward, right? All with the use of Lois. And it’s like all of sudden this magnificent attorney can now clone himself in a way and make sure that he can do all of the things the best way possible. In the past, what that looked like is, hey, get out there, do a good job in that deposition, make sure you get them to say this.
And hopefully that’ll get us what we need to do or like the outcome that we need. Right. And it’s like, now we can actually almost guarantee that by giving them the right coaching pre, during and post because of it.
Beau Hamilton (24:14.75)
That’s incredible. It’s like the ripple effect from this software is just mind boggling to think about. And every, mean, I hear a lot of these examples in all these different industries and hearing about what this is doing for litigators or one particular one lawyer. you think of all the lawyers and litigators using this platform. mean, again, the ripple effect is astounding to think about.
I also want to think what fascinates me too is how you’re able to cater the platform across a wide customer base, right? Cause you’ve got, I imagine you’ve got small firms, got massive in-house teams, you’re working with government agencies, you’ve got prosecutors, public defenders. I mean, the list goes on and there’s all these different environments that you have to kind of cater to. And then usually when a platform
tries to be everything to everyone. It kind of ends up being watered down, kind of mediocre for a lot of them. So I’m curious, like, how do you build one platform just flexible enough for all of these different clients without, without watering it down.
Keegan Chapman (25:21.346)
Yeah, this strategy started really early. when case management platforms originally came out, a lot of them built templates and asked the attorneys to fit into what they think the perfect flow for whatever that kind of practice of law is. And so what happened is you saw a lot of siloing or a lot of softwares that could kind of serve only the SMB market or only the enterprise market or whatever it might be. Filevine took a little bit different approach, which
I think is a big reason why we’ve been able to apply AI in the way we have. we said, no, we want to make this customizable and configurable from the start. You don’t fit into our platform. We build a platform that fits into the way that you’ve been Uber successful as a legal professional. What that allowed us to do is create all of these different modules at the core, different API integrations for those that have other softwares that need to come in based on whatever area they’re in. And we found a way to orchestrate that all together as one.
core system of record or data source. Well, when you have that, then you can lay your AI on top and serve anyone. we serve your right. We can serve your one person attorney shop that just or legal shop that just opened. We could serve your in-house counsel. I mean, we have amazing in-house counsel groups putting, you know, 10,000 contracts across their teams in any given year. We have government agencies. We have
know, state and local departments. have enterprise firms that have six or seven, maybe 15 different practice areas. And we work with them to make sure that those core, that core infrastructure underlying looks like something that can pull in everything they need for the context to then serve the AI. The AI can then, because of the way we built the vectorization model and the way we brought legal language in, can then work within those spaces based on the data it’s provided.
And so not easy, right? But we’re once again doing the harder thing. It’s a lot easier to have a template. But that’s kind of the core piece. The second thing we did, from the very beginning is took security very seriously. So we have enterprise level, some people say like bank grade, government grade security, all the way down to the smaller mom and pop legal shop that’s serving people in their local community that’s super important.
Beau Hamilton (27:21.654)
Of course, of course.
Keegan Chapman (27:47.2)
and never would have even thought about that. We apply it everywhere and anywhere to make sure that they are, anything they are putting in that system, which often happens to be quite a bit of very sensitive data, is safe, regardless of how they’re using it, serving it up and working with their team. And so I think that’s also allowed us to expand into this government space and this corporate space where there’s really high stake matters.
And we need to make sure that they feel that every bit of information that is going into the system is going to be safe. And then if they’re going to use AI on top of it, it’s going to stay safe.
Beau Hamilton (28:21.006)
Well, again, I think that’s, it kind of goes back to you really thought about the problems from the beginning and you, you, wrote a, you started from a, you rewrote the platform from the ground up around the scale problem and, how AI is going to help, help tackle some of these, these problems and offer solutions. And I think that a lot of the, you know, software platforms in this industry or other industries that are just sprinkling in the AI features on top of kind of their, current platform.
They’re gonna have to come to that that point where they’re gonna have to start rethinking Fundamentally and the fact that you guys have already rewrote the platform It just you guys are added definitely a much bigger advantage, right because you don’t have to Go through that arduous process Which is you know easier said than done it takes imagine it it took it took quite some You know, it’s a lot of long nights
getting all that code updated and incorporating all the features you want to incorporate. And I’m sure you got a long laundry list of other things you want to add to, but.
Keegan Chapman (29:28.012)
Yeah, the AI team, machine learning team, engineering teams, they are phenomenal. mean, though, they are pushing code. It feels like every minute these days. It used to feel like every day. But stuff can happen faster when you leverage the right tools in-house as well, and you have the right experts in-house to guide these conversations. I think you’ve probably seen we’ve had a few acquisitions over the last year as well.
Beau Hamilton (29:38.445)
Yeah.
Keegan Chapman (29:54.104)
Some of the reasons we acquire is obviously they have great tech, but then also there’s been amazing talent that has come from those acquisitions to help bring us forward in this, what we’re building, helping us think farther. We have a full legal futurist team that purely looks at what they think will be needed in the next three to five years. And we try and start building it now so that that way our software always stays kind of a step ahead for the people we’re serving who are serving so many great people in the world too.
Beau Hamilton (30:23.64)
So I want to flag this, the stat that I came across that, cause I think it connects to everything we’ve been talking about up until this point, but it’s, it’s, comes from Reuters Reuters reported that file vine is now making more money from its AI products than from the traditional software platform. And that caught my attention because, you know, we’re not talking about a startup that launched as an AI company that is, you know, a shift that has happened. There’s been so much talk about all this capital being thrown into AI to build out.
data centers and software platforms and all the money that companies are allocating to AI, hoping that it pays off, but still years away from it actually paying off and actually generating a revenue that backs up their investment. But it sounds like it’s already starting to pay off with you guys and with Filevine, which I think is very exciting. Does that, you know?
I think it goes without saying, but like, does that signal just where legal tech is heading, you know?
Keegan Chapman (31:23.828)
Yeah, it’s interesting. It’s not just a milestone, right? I think the whole world’s heading in this direction. if you don’t, you know, pull in a personal anecdote, but my dad always says, like, you, the biggest fear we should all have in the world is becoming irrelevant. And with the rise of AI, you can become irrelevant with a blink of an eye, right? And so the way I think about it, the way our team thinks about it is this is signal that no one
no longer wants just insights, right? They want better outcomes. They are willing to leverage what’s right for them to get that. And that context to have those better outcomes is the most important part. And so I think that’s like the first core of it is like, everyone’s going this way. You can either fight it and say, we believe that the old way is still the same way. I think about this when we trying to get people to go on the cloud with Filevine many, many years ago and people still wanted on-prem solutions, right? Like we…
We did Era One, now we’re in this new one. But the other thing is too is people are willing to pay where they can get the outcomes, right? And so what happens is you provide the right solutions and you’re a trusted source, right? Like law firms, legal professionals have been trusting Filevine for a really long time. So we get the opportunity to show them how we think it should be done. And luckily,
We personally have a ton of context, right? We didn’t just pop up two years ago and say, we’re going to solve the legal AI problem. We’ve been solving legal problems for so many years, and now we get to solve it in a new way. That’s a fun challenge to have. So what happens is you’re trusted, you have great products, those products can serve those people very quickly, and they start to see the outcomes out of the gates. It’s kind of a no-brainer at that point.
Beau Hamilton (33:14.072)
Totally. Yeah. Well, I love that quote that your dad provided. And it just makes me think too of, know, again, it’s like we hear this frequently, but it’s AI is not going to take your job. It’s someone who’s utilizing AI is going to take your job. And the same is true with companies and organizations, the companies that adopt these new tools and work to incorporate them in a way that ultimately maximizes the valuable outputs. That’s really, they’re the ones that are going to
be successful and set themselves up from the failures out there, the companies that don’t adopt and kind of stay stagnant. So I want to get to, I want to go a little bit more big picture and just maybe we could talk about where all this is going. mean, I know AI is all the focus right now. We’ve heard a lot about agentic AI and having these tools actually act upon
act on the user’s request and carry out tasks for them. Where is this, where’s AI going in this field? Where is it all headed? In the next six to 12 months, what are some of your main sort of checklists of things you’d like to incorporate into the platform?
Keegan Chapman (34:35.852)
Yeah, I think the people that determine this are our customers and the users of AI, which is always really fun. I notice that people will come into the platform or even come to Filevine. We have lots of new potential clients that come in and say, I just want an AI solution. I don’t want a ton of change management. I want to be able to try it today. And then I’ll think about the bigger picture. So it all starts somewhere.
The way I’ve described it to my team is no one wants to change their entire persona and wardrobe right out of the gates always, right? They want to maybe try on a new shirt, see how it made them feel. And then from there, they may kind of invest more heavily into kind of how that’s going to help them. So we’ve created a way for people to come in and be using Lois within a day, right? Like they can upload a document. They can see the baseline of what a really good
highly secure, legal specific AI can do for them. And that’s kind of like step one. What happens 99 % of the time, Bo, is they say, is there a better way to get everything in here so it can start thinking with me? And so that’s when people start to say, let’s leverage all of the power of Filevine. They end up wanting to make sure that all of their tasks are there, their emails are rolling in, their documents are there. So the customer then determines, OK, now I want it to be able to think with me.
Well, I think where it’s going next, is can it think before me because I have everything there. So some of the questions customers have said to us are, if I came in and I sign into Lois in the morning, could Lois automatically surface everything I probably should have thought of last night so that I can start my day stronger? Or…
hey, is there a way that I can proactively have certain things, agents pulling and doing certain things in the background so when I get to that point, it’s already served up and ready for me? Are there ways for it to be more in the moment with me versus where AI started, which was a lot of time like post action analysis or summary, et cetera. And so that’s kind of where we’re headed, Bo. mean, the list is endless. This AI…
Keegan Chapman (36:48.046)
capabilities and what agents you can build. I mean, we could think of everything in the world, but I think that’s like kind of phase three, which is how are we making sure we’re serving up those things proactively versus making the AI only a reactive source of truth for folks once they’ve done something else.
Beau Hamilton (36:53.816)
Yeah.
Beau Hamilton (37:07.608)
Yeah, absolutely. Be more proactive, less reactive. I think that the visual I think of when in that answer is, when you, you know, I think listeners, when you interact with your chatbot of choice, your customer facing chatbot, chat, GPT, Claude, Gemini, you name it, you know, when you get an output from your request, let’s say it’s like tracking up, I don’t know, the price of Bitcoin or something. It’s like, it’ll generate a lot of times it’ll generate a follow up question. like, well, if
If this is helpful, if it’s helpful, I could also generate a dashboard so you could just go to this webpage and see this. or I could, you know, send you text alerts when it gets, you know, above a certain point or whatever. It’s like questions that it tries to predict your next question and your next intent. And a lot of times like, you know, you don’t have, I wouldn’t have thought of that necessarily, or at least I would have thought of it later, but it’s kind of start starting to, you know, get inside my head and start thinking about useful next steps.
Keegan Chapman (37:40.354)
Mm-hmm.
Keegan Chapman (37:48.45)
Mm-hmm.
Beau Hamilton (38:01.632)
And so if you apply that to what you guys are tackling, I’d see how that would be, you know, that would be the next big, you know, proactive move. so it makes a lot of sense. I’m just excited to, I’m going to have to, we’ll have to have you back, you know, in the, in the coming months or a couple of years just to see like what, kind of changes, I’m, things are moving so fast that it’s, it’s really difficult to say exactly where things will be, you know,
Keegan Chapman (38:26.446)
I was going to say, well, you could have me back in probably two weeks at the rate we’re going and I could tell you something new that we thought of because of an amazing customer story. I mean, we’re really lucky. Our customers have been so along on this journey with us. I mean, I was out, flew out to California and got to meet with one that I mean, he used AI in a massive case. And on one side of the courtroom, there was 18 of them, 18 people flipping through binders, freaking out, Googling things, trying to figure out what their case strategy was.
Beau Hamilton (38:29.792)
Right? I bet.
Keegan Chapman (38:56.364)
and he was on a team of three with Lois and he won. Okay. Like there’s just so cool. It’s such cool stories that when you actually get in with them and you can start to figure out why they leveraged it, when they trusted it, how it was helpful, where we could improve the product. We do a ton of that because we believe that the people on the front lines are the ones that are going to help us build exactly what they need. We have ideas.
Beau Hamilton (38:58.83)
Wow. wow. Yeah.
Keegan Chapman (39:23.074)
But usually those ideas are really solidified by those experiences that those attorneys and legal professionals share with us.
Beau Hamilton (39:29.538)
I love that. Yeah, I love hearing the concrete examples to help kind of, you know, paint a picture of the solutions. That’s awesome. They won the case. OK, well, I want to pivot slightly and just shift gears to get into some rapid fire leadership stuff before we wrap up. Now, Keegan, I know every every leader I talked to has that one thing they wish the market understood, the thing that you’d like, maybe shout from the rooftops if you could.
Keegan Chapman (39:37.634)
Mm-hmm.
Beau Hamilton (39:57.614)
So if a prospect is listening to this right now and they they can only take away one thing about Filevine or maybe the industry as a whole What would you want them to know?
Keegan Chapman (40:07.916)
Yeah, I think it is that your AI is only as smart as the information you give it. That’s how it lives today, right? And so when you’re evaluating which AI partner to go with, think about where are they getting their information? How are they making sure it’s in the right place so that when you’re ready to ask those questions, look for those insights, create those outcomes, that it’s coming off of data that you trust and you know is going to provide you the best possible answer.
Beau Hamilton (40:34.422)
Now you’re in a space with a lot of noise, of course, a lot of companies making big promises right now. What’s something your competitors are getting wrong that you’re determined to do differently?
Keegan Chapman (40:46.146)
I think right now in the industry, many of the other solutions are trying to solve one or two problems. I was talking to a potential prospect that was using another AI solution in the market and they said, you know, they came in and they told me they could solve for this. So was really excited because that was the problem I had that day. Now after months of trying to use the software, I realized that the carpet isn’t running from wall to wall.
I have spaces and gaps that aren’t helping me actually become more efficient or drive a better business process around AI. And so I think that’s kind of where many are missing the mark is they’re coming out and they’re promising a lot. They’re solving one quick problem. But once those software or once that AI is being implemented, the users are realizing it wasn’t just one point in time they needed to fix. They needed to think about how they can leverage AI across their entire workflow.
to ensure that they’re getting the right answers and that people can be more efficient or do better work or whatever it might mean for their organization.
Beau Hamilton (41:46.126)
I love that. All right, great answer. All right, well, last question, last really substantive question, and it’s going to be a little bit more personal. apologies. I won’t throw you on the spot, you know, that’s true. It’s true. Well, we’re, you know, leading through a period like this is challenging. It’s moving so fast. It’s a lot of these AI advances, of course. The expectations, they keep climbing.
Keegan Chapman (41:57.762)
I mean, I’m telling you about my dad already, Bo, so we’re okay.
Beau Hamilton (42:12.834)
How do you stay motivated and just keep your team motivated during these tough stretches, these long nights and all these, you you have to communicate with everybody, keep everyone in the loop. What are you doing to just keep everyone in the right head space?
Keegan Chapman (42:27.532)
Yeah, I think it’s a matter of taking challenges and looking at them as opportunities. What a cool time for all of us to be creating, figuring things out, building new software AI. I think about I lucked out. I got to work for Groupon when it was the fastest growing company in the world. Right. Let me tell you about it was not always the most motivating feeling. was not always not. It was almost always stressful. It was always almost
challenge just to help people understand what we were trying to build because there was nothing like it, right? And so I take that at my core and I think about, how does that apply to what we’re doing right now? And it’s like, we have an opportunity to change the way people work. We have the opportunity to provide them with tools to actually serve these people who need help better than ever before, right? The attorneys we are serving,
They made a promise that they will use the right tools, the right resources, the right access to help serve their client in the best way possible to provide them the best outcome in whatever that case looks like. Whatever side of the courtroom they’re sitting on, it does not matter. And I think if we can get our heads out of sometimes all the tasks it takes, all of the stressful conversation, all of the high confront feedback, all of the moments where you might feel like you’re doing it wrong, and then think of this instead as an opportunity where it’s like,
we get to make this up. We get to leverage our customers’ experiences and build something that’s never been built before. So anytime we get too tactical, and in marketing and sales, that’s easy to do, right? It’s like, I need to make calls, or I need to write this one pager, or I need to make sure the website’s up to date, or I’m going to post an ad online. It’s like, okay, we got to think bigger than that. What we are selling and what we are offering to the market is going to change the way they serve their clients.
Beau Hamilton (44:07.394)
Yep.
Keegan Chapman (44:21.644)
and honestly change the justice system if we do it right because we’re going to help people get better outcomes, which is a pretty powerful moment if you can get your head out of this stuff is hard today.
Beau Hamilton (44:24.483)
Yeah.
Beau Hamilton (44:31.414)
Yeah, yeah. man, that’s such a great answer. And I love the big picture focus. And, you know, I think the daily tasks, they are important. mean, you got to, you know, you got to grind and stick it through to get to accomplish those big picture tasks. But, you know, at the same time, you could see it absolutely helping you by by keeping your eye on the prize and not getting overwhelmed in the, you know, the present with all the the to do’s that are keep, you know, the long list of
of actionable items.
Keegan Chapman (45:04.014)
But one time I had, sorry, it just made me think of this. I had a leader early on in my career say to me, you know, when you look back on what you were doing, is it what it says on your resume or what’s actually more important could be what’s the story you wanna tell? And anyone that is working in AI right now is going to have a kick-ass story to tell, right? It’s like, think about 10 years down the road, like.
Beau Hamilton (45:27.48)
Yep.
Keegan Chapman (45:30.69)
I don’t even know what’s possible. You don’t know what’s possible. I mean, we were joking even in three weeks, this is going to look different. Who has the honor of getting to work in that space and say, this is what I learned. This is what I created. And now whatever takes over AI in the next 10 or 15 years, we get to go apply that again and then be at the forefront of whatever the next generation of technology is. mean, we’re in like a very exciting place to work.
Beau Hamilton (45:57.55)
Totally. Yeah. mean, another quote I thought of a two is like, when you’re when you’re born, you know, you look like your parents when you die. You look like your decisions. Right. And if that’s not motivational. Yeah, I think I love I love you just made me think of it. So I appreciate that. But I’ve been thinking a lot about that and just, you know, yeah, look at the big picture. Look at the ripple effect of your decisions, how you’re who you’re influencing. I mean, that’s one of the the
Keegan Chapman (46:07.662)
I’ve never heard that, that’s awesome.
Beau Hamilton (46:25.868)
many reasons why I love, you know, talking with people like yourself and just hearing about your insights and delivering this conversation to our listeners, you know, and having the ripple effect that it, that your information has on them. So with that said Keegan, thank you so much for all the insights. If, is there a link listeners can visit to learn more about Filevine or get in contact with your team or maybe a resource you’d recommend they explore anything at all?
curious.
Keegan Chapman (46:56.578)
Yeah, I mean, the best place to send them always is our website. We have everything and anything you could ever want to know about the core infrastructure of Filevine, as well as all of the AI we’ve built throughout, the new agents coming, and how we can help serve anyone in the legal industry, regardless of if you’re at a firm, you’re in-house, or at a government agency. We will have great people to talk you through kind of what the right solution is, or help you think through how to evaluate AI for your…
practice or your business so that you can make a really informed decision, whether that’s us or not. But our hope is we can help people pick the right things and be successful and get the outcomes that they want.
Beau Hamilton (47:38.318)
Amazing. All right. Keegan, thank you again so much. Thanks for this conversation and for breaking this all down with us. I appreciate it.
Keegan Chapman (47:45.516)
Awesome, thank you, bye.
Beau Hamilton (47:47.054)
All right, thank you all for listening to the SourceForge Podcast. I am your host, Beau Hamilton. Make sure to subscribe to stay up to date with all of our upcoming B2B software related podcasts. I will talk to you the next one.