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8 Sep 2026 · 45m · 15 chapters

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Casefleet Founder Jeff Kerr on Fact Management in the Age of AI

In short

CaseFleet founder Jeff Kerr discusses “fact management” for litigation, focusing on chronologies, and how CaseFleet’s AI agent Casey accelerates building case timelines with accurate citations while keeping AI “read-only.” He also explains CaseFleet’s move back toward e-discovery workflows and how specialized litigation tools may survive even if frontier AI labs go downstream.

Guest backgrounds

Jeff Kerr is a lawyer (graduated 2010), practiced employment law, left practice in 2015 to found CaseFleet. CaseFleet has been profitable since 2018 and grew without outside capital.

Key claims

Chronologies are crucial in employment cases; AI reduces chronology creation from ~10 hours to ~10 minutes. Casey drafts/recommends but cannot file, send, or act; citations are structurally prevented from being fabricated via exact-text matching. CaseFleet is “agentic” in tool-iteration sense, not consequential-action sense.

Notable examples

Employment retaliation/demotion timeline; medical negligence example with negligence elements and sub-issues; AI-generated 23 facts with clickable orange-highlight citations.

Written by AI. May contain mistakes.

Chapters

2:59

Introducing Jeff Kerr and CaseFleet

Discussion about Jeff Kerr's background and the founding of CaseFleet.

“I am looking forward to this conversation.”
3:30

The Evolution of Case Management Technology

Exploration of the challenges faced in law practice and the need for better technology.

“I mean, you were a practicing lawyer, and CaseFleet kind of grew out of problems you were encountering in your own practice.”
6:10

The Growing Importance of Chronologies

Jeff discusses the critical role of timelines in legal cases and their increasing relevance.

“And chronologies are very important in employment law.”
8:00

Challenges of Fact Management Tools

Discussion on the time-consuming nature of creating chronologies and the impact of AI.

“And I feel like I have a pretty good theory as to why this type of product is becoming cool again.”
10:30

Transitioning from Practice to Tech Startup

Jeff shares his journey from practicing law to founding a technology company.

“What was it like to suddenly become a founder and a CEO and building a tech company?”
14:00

CaseFleet's AI Integration and Workflow

Learn how CaseFleet integrates AI to enhance the legal document review process.

“Motion sensing, I'm just going to light them up again.”
26:59

Understanding Agentic Tools in AI

Explore the concept of agency in AI tools and its implications for users.

“you've talked about Casey as an agentic tool.”
28:00

Understanding Agentic AI in Legal Tech

Learn about the concept of agentic AI and its limitations in legal tasks.

“an AI system that receives some starting point guidance from a user or a quest.”
30:08

New Features of CaseFleet: Drafting and Citations

Discover how CaseFleet's AI enhances drafting and citation accuracy.

“Another one of the big ones is drafting.”
32:01

Semantic Indexing: Enhancing Document Searches

Explore how semantic indexing improves document search capabilities.

“And so, you know, I haven't tested every single AI tool on the market, but the drafting inside of CaseFleet is very cutting edge and very powerful and constantly surprising me.”
Show all 15 chapters
34:08

CaseFleet's Role in e-Discovery

Learn about CaseFleet's capabilities and features in e-discovery.

“which means it's not vulnerable to the fact that maybe this person didn't use the exact keywords that you're thinking of.”
36:01

Competitive Landscape of Legal Tech

Gain insights into the evolving competitive landscape of litigation technology.

“and expect that to be done within the next year.”
38:24

Funding and Future of CaseFleet

Understand CaseFleet's financial position and future growth expectations.

“You know, it's interesting at our company, we always have a list of things that you kind of want to do when you have time.”
42:00

Future of Litigation Tech and AI Impact

Discussion on the anticipated future of litigation technology and AI's role.

“Our team has grown a lot, but we just want to keep doubling down on what we're doing here.”
43:40

Ethical AI Development at CaseFleet

Jeff Kerr shares CaseFleet's commitment to ethical and responsible AI usage.

“I'll read the same type of 10 times and not see it.”
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Transcript

Automatic transcript. May contain errors.

0:02LawNext Host: Welcome to LawNext. You might say that chronologies are having a moment in legal tech. A number of AI startups now pitch litigators on turning a messy evidentiary record into a structured timeline in minutes. I guess today was doing that more than a decade before any of them. Jeff Kerr graduated law school in 2010, hung out a shingle in employment law, and then left practice in 2015 to build CaseFleet, a case management platform for litigators. The company has been profitable since 2018 and until now has grown without outside capital. But even though CaseFleet was early to market, that has not kept it from embracing AI.

0:45LawNext Host: Last month, the company launched Casey, an AI agent that builds a case chronology through a conversational interface with a citation engine that Kerr says makes fabricated citations structurally impossible. Kerr draws a hard line on agentic AI. Casey researches, drafts, and recommends, but it doesn't send, file, or act. And CaseSleet is edging back toward e-discovery, market Kerr tested but abandoned early on. We talk about all of that, plus what happens to specialized litigation tools if the frontier labs decide to come downstream. I'm Bob Ambroji, and this is Law Next, the podcast that features the innovators and entrepreneurs who are driving what's next in law.

1:29LawNext Host: And a note, if you are listening to the audio version of the podcast today, you may want to switch over to YouTube and catch the video as our conversation includes a visual demonstration of some case fleet features. Before we get to any of that, please take this moment to hear from the sponsors who so generously support Law Next.

1:53LawNext Host: This episode is brought to you by Briefpoint, the discovery governance and automation platform used by more than a thousand law firms. Briefpoint just launched Discovery Playbooks. Here's the idea. You respond to Discovery like you always do. Save it to your playbook in one click. And the next time a matching request shows up on any case, BriefPoint reapplies your objections and response strategy automatically. No data entry, no setup. Watch the 60-second demo at BriefPoint.ai. Whether you specialize in workers' compensation, employment and labor, or insurance defense, Marist Case is the legal practice management software tailor-made to your law firm's specific needs.

2:40LawNext Host: Best-in-class features like document management, time tracking, billing, and online payment reconciliation helps you automate your practice and streamline your workflows. Discover how Merus Case can level up your practice and reduce your administrative workload by visiting meruscase.com. That's M-E-R-U-S-C-A-S-E dot com. Now let's get to today's conversation. Jeff, welcome to Law Next. Thanks, Bob. Great to be here. I am looking forward to this conversation. We haven't had a chance to talk in a while, and I know you guys have been very busy at CaseFleet over the last year or so. Before we talk about any of that, I kind of want to go back and get the background on you and the company.

3:29LawNext Host: So let's go back to the beginning. I mean, you were a practicing lawyer, and CaseFleet kind of grew out of problems you were encountering in your own practice. right?

3:40Jeff Kerr: Yeah, that's right. I graduated law school in 2010 and made the kind of crazy decision to start a law firm as my first job out of school. So a friend of mine from school and I started an employment law firm and we were taking cases and figuring out how to do them. And one of the cool things about having my own practice was that I got to choose which technology we used. And so we were constantly experimenting with what's the best practice management software we can use. How can we better do our intake process? And so there was a lot of legal engineering in my career, even when I was just beginning my practice.

4:28Jeff Kerr: And I'm one of those types where building anything, even something inside of an Excel spreadsheet was kind of addictive and not just snowballed as I was practicing. And once I was at about five years in, as much as I loved working my cases, I was much more interested in building some type of technology tool for practicing lawyers. And I realized that to do it to the extent that I wanted to and to make the product of my dreams. I needed to make it a full-time endeavor. And so I left the practice in 2015 and started CaseFleet. Our initial office was the same office that I was in. I was just sort of became a sublessor of the space inside my firm.

5:15Jeff Kerr: And it's been a great journey.

5:19LawNext Host: Did I read that you taught yourself to code as well as part of that?

5:23Jeff Kerr: I did. I had experience writing code when I was in high school and I was really good at it, but then I didn't touch it for more than 10 years. And so I knew that it would probably come back pretty quickly. I was just doing some programming exercises nights and weekends and it came back and that's been a lot of fun. Yeah.

5:43LawNext Host: Well, I mean, obviously there are a lot of problems that you can encounter in the course of a law practice and a lot of different kinds of technology, but specifically, what was it that you kind of wanted to tackle with CaseFleet when you started the company?

5:56Jeff Kerr: The top priority for us was always fact management. This, for me, was the key to success in my cases, was knowing the chronology of the case cold. And chronologies are very important in employment law. Sometimes you have an employee who makes a complaint that's protected under federal law, and then they get demoted or fired soon afterwards. And the employer's story is that there was some kind of problem with their work performance. Your story is, no, the real reason for that was the fact that they made this complaint. And so you really have to know the entire timeline of the case cold. and not just know what the facts are, but how you're going to prove each one of them.

6:46Jeff Kerr: And we wanted to make that easier for people and give people a better way of doing that than just having a Word document sitting in their folder that kind of outlines everything. It's hard to collaborate with a Word document. It's hard to capture the relationships between facts and evidence in particular.

7:06LawNext Host: Yeah, I actually used to do some employment litigation back a long time ago in my career. I understand the idea that timing in itself can be evidence often when one action follows another in close succession and there's kind of no other explanation other than that one happened right after the other, right? I mean, that's kind of the way it works in employment litigation. It's interesting because chronologies have become, over the last year, it seems like, over the last couple of years, suddenly they've become a very hot topic. I mean, I know there has always been software, you know, yours and others that have attempted to solve the chronology problem.

7:48LawNext Host: But it's been interesting to me to see how much that particular issue has kind of come to the forefront over the last couple of years with a lot of companies focusing on that. You were maybe a little ahead of your time with that.

7:59Jeff Kerr: Definitely. And I feel like I have a pretty good theory as to why this type of product is becoming cool again. up until the AI revolution began, making a chronology and a tool like ours actually took a lot of time and effort. So you have to go through the evidence and for every fact that you add to your chronology using, for example, the legacy version of Case Fleet or the legacy version of Case Map or any of the other companies in the field, It's a lot of clicks. It's a lot of entry and form fields. And so you do create this extremely useful thing at the end. But the process of getting there, it's just a hard sell to a lot of people to say, look, you'll be very happy.

8:56Jeff Kerr: It'll pay dividends. But this is going to take 10 hours of work on each of your cases. With the current capabilities of AI systems, AI just makes all of that. infinitely easier talking a reduction in time to create a chronology from 10 hours to 10 minutes and so suddenly this is a much more compelling option and i i think everybody always knew that having a really well organized chronology was a good thing and something that you would want

9:27LawNext Host: it's just it's easier now yeah yeah and yet and yet that the the problem hasn't changed i guess i I mean, it's all about taking that messy record, evidentiary record that you have and turning it into something that you can use in a more structured and easily navigable way.

9:45Jeff Kerr: Yeah, fortunately, the data model for what a chronology is, is the same as it was 10 years ago. You've got facts in your chronology. Those facts are connected to legal issues or else they wouldn't be important and you wouldn't want to put them in. And the facts also have a connection to evidence and to different actors, witnesses, parties, business organizations. They're sort of the things that play a role in the facts. Yeah.

10:18LawNext Host: So, again, just before we leave those kind of earlier days of the company, just curious what that experience was like for you to go from practicing law to starting to build some technology to turning that technology into a company. What was it like to suddenly become a founder and a CEO and building a tech company?

10:44Jeff Kerr: I'd say it was very humbling. With the law firm, you can hang up a shingle. And if you do a good job representing your clients, you can start making a living very quickly. With a software product, you have to build something that's extremely useful before anyone's going to pay you for it. and I think I was probably a little overly optimistic in terms of how quickly the company would grow at the very outset. And so, you know, it was more of a sort of slow and steady growth curve for us and also really refining what our product offering was. We, in our very first year of operation, made a little bit of a mistake and were like, Let's also do practice management and e-discovery and bundle these things all together with the timeline product.

11:40Jeff Kerr: That's just doing too many things at the same time. And when we pivoted and just said, hey, look, the company is about fact management. That's when we hit our stride, which was in about 2017.

11:54LawNext Host: I came across something you posted on CaseFleet's website from, I think it was like 10 years ago or something, from how I, your early days in legal tech or something like that was an article that you had written, but you talk about going to, Craig Ball encouraging you to go to an eDiscovery conference and getting somewhat, I think, inspired and motivated by that. But yeah, that is a lot to be combining eDiscovery and everything else into one product.

12:21Jeff Kerr: Yeah, eDiscovery has always been in the background for us. It's something I'm personally very passionate about. In my career practicing, I had this incredible string of cases that were all won because of e-discovery. By pushing really hard, knowing what to ask for, knowing how to deal with native files, I would uncover evidence that would essentially prove my client's case to the point where the other side was just compelled to settle for exactly what we were asking. And we've always wanted to play some role in helping people be able to do that more often without spending the kind of money that big corporations are often spending on e-discovery.

13:13Jeff Kerr: So there's still a little bit of a twinkle in our eye about e-discovery. And our product increasingly does some really useful e-discovery type of workflows. And there's more coming in that way in the near future. But, you know, the core of the company is still fact management. Yeah.

13:30LawNext Host: So, you know, you talked about the fact that a chronology that at one point might have taken 10 hours is now 10 minutes or whatever you said exactly. So how has that affected your product? How has your product evolved from what it was you built all those years back to what it is now?

13:52Jeff Kerr: So the great thing is that we haven't had to change the classic version of CaseFleet at all. Pardon the lights here. Motion sensing, I'm just going to light them up again. Okay.

14:11LawNext Host: It's funny because I thought it was darker in his room or was that just me?

14:15Jeff Kerr: It suddenly did. Yeah, it's on a timer here. and you know we have very passionate users of classic case fleet and we didn't want to take that away from anyone and so we never wanted to change our product so that you had to use AI. AI is something that literally sits alongside the classic case fleet and drives all parts of classic case fleet if that's the experience that you want to have. We're big believers in having long-term relationships with our customers. We're not going to pull the rug off from anyone or change the product and turn off some workflow that they depend on. But AI has fit very nicely with that core suite of tools and has just been a great match.

15:11Jeff Kerr: So it's not one of these things where it's like bolted on as an afterthought. And just because you need to do AI, we always knew that it was going to be amazing if wired up correctly. And I think we've been able to achieve that in the last year.

15:26LawNext Host: How does the classic experience differ from the AI enhanced experience or maybe put it the other way around? So I can show you. uh well we can't we're putting this out as a podcast so it's also just audio so uh okay we have video here but most people will be listening to an audio so perfect so let me let me walk you so you can you can tell it you can make it paint a picture in words if you want perfect um should

15:57Jeff Kerr: i also share my screen um so that anyone who's watching it can see and i'll be talking along or

16:03LawNext Host: If you want to do that, that would be fine. Sure.

16:07Jeff Kerr: Great.

16:13So the classic Ace Fleet workflow for creating your chronology would start with uploading documents. You can upload PDFs.

16:25Jeff Kerr: We sort of specialize in PDFs, even very obnoxiously long PDFs, let's say. Let me just stop for a second.

16:32LawNext Host: stop here for a second, but only because you've got, we've got like a little window showing our, there you go. Okay.

16:38Jeff Kerr: Is that better? Yep. Yeah.

16:43Jeff Kerr: So, CaseFleet, first step in creating the chronology would be to upload the documents for the case. These could be deposition transcripts, PDFs, leadings, native format, emails, any type of document that might have facts inside of it. We then have a built-in document reviewer. Once the documents are finished processing, scan for viruses, metadata is extracted, and you would open the document in our document viewer, read the document, and when you find text that points to a fact or that is a fact, you highlight it, choose create fact from a little menu that appears that any dates that are in the text that you highlighted would automatically be pre-filled for the date for the fact then in this form you choose the issues that the fact relates to and you can at mention by hitting the ampersand key on your keyboard to link to an entity in the memo area for the fact.

17:56All right.

17:56LawNext Host: So just for people who might be listening, not watching, you started in kind of the case, the matter management page, I guess, and you showed how you could upload a document there. Then you opened the document. And as you just said, you've highlighted a passage within that document, and then that opens up a little form on the side of the screen with the fact preloaded into it. And then your ability to add in these other details about date and type and those kinds of things. Yeah.

18:27Jeff Kerr: So the core workflow really centered around reading documents that you're going to have to read in any case and then performing this very natural action of highlighting the interesting parts. And with a few other clicks, just hitting save after you've highlighted, you'll be adding facts organically to a chronology as you work through your document review yeah yeah so that's classic case fleet which is still supported and has many dedicated users who are a huge fan of doing it that way the new way of doing this in case fleet is to drive the process us with Casey, who is our AI agent. It's available.

19:16LawNext Host: And Casey is the AI agent you just announced this month, right? That's correct.

19:21Jeff Kerr: Recently, last month, I guess it was. It was out for a couple of months. Yeah. Okay. With the generic name of AI Assistant. But it's the user interface of it got overhauled. It's now got a friendly name, which kind of matches how people were interacting with it even before. And it's a completely conversational, natural language type of interface familiar to anyone who's used ChatGPT or Claude or Grok or any of these types of tools. And when you open a case, it will actually walk you through the process for opening the case. So open a new case, case you will appear, recommend uploading documents as you're uploading them it'll begin reviewing them and putting in place some of the foundational components of a case and case lead so the main foundational component would be your your issues tab so i've clicked into that in the interface right now and it's showing us what the important legal and factual issues are in the case

20:33LawNext Host: Okay, this example is a medical negligence case. Exactly.

20:38Jeff Kerr: So if you wanted to be real simple about it, you might have a negligence case, and it's got the four classic elements of negligence, causation, duty, breach, and damages. is most people are a little more detailed than that. And so they'll include different themes or keystones for what the breach might be. In the case that I have loaded in right now, it's sort of a failure to diagnose medical malpractice case. So there's a delay in neuroimaging sub-issue. There's one for failure to consider a CSF or spinal drain. And once these issues are in place, the AI then knows as it's reading your documents and performing other tasks, what the legal framework is, and it's able to build on top of that.

21:36and going back to chronologies,

21:39Jeff Kerr: which is really what Caseload is all about. We have this core agentic workflow where the agent understands that creating a chronology is generally everyone's goal on the platform, but it'll walk you through this order series of steps. It starts with creating this issue structure and then you can give it guidance on what type of facts you want it to propose or in this example I've got pulled up right now I just said propose facts the Casey will get that direction and then start researching reading documents and structuring facts to be inserted into your chronology. So in front of me, I've got 23 facts that have all of the attributes of facts that would be created by an expert human user of CaseFleet in the pre-AI days, except that the amount of time to do this was less than 10 minutes.

22:54And the beauty of the data model here is that for each of these, we can open up the fact and we have these citation links.

23:07Jeff Kerr: So the citation links are guaranteed to be accurate. It's actually not even possible for the AI to create them if they don't match to exact text inside of the documents that they refer to. and better than that you can hit a little launch button for a citation it'll open the documents and it will highlight in orange the exact text on the page that the AI is citing for the proof for

23:39LawNext Host: the fact so somewhere I I think it was in something you put on LinkedIn I saw you post something to the effect that you're not selling faster as you are better or something along those lines. That speed isn't ultimately, being able to do this more quickly isn't ultimately the goal so much as being able to find things maybe that you didn't so easily find before. Did I get that

24:08Jeff Kerr: right or is that your feeling about it or you know I'd say that speed probably is a part of it being efficient in this workflow you know the original workflow just it took a significant amount of time to do all the highlighting and I think that clients expect people to be able to process a significantly large document corpus faster today. And so we want to help be part of that story. But the way that the assistant works, it's not replacing the attorney in any way at all. Instead, it's helping you do your work in a way that allows you to focus on what really matters. The higher level strategy for the case and the minutiae or the busy work is what the AI is handling.

25:07LawNext Host: Yeah, that makes sense.

25:18LawNext Host: Even as CaseFleet integrates AI, Jeff says he draws a line between AI that recommends and AI that acts. In a moment, we'll talk about that line and why CaseFleet won't cross it. We also talk about why CaseFleet is moving back toward e-discovery a decade after walking away from it. But first, please take a moment to learn about the sponsors who so generously support this podcast.

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27:36LawNext Host: you've talked about Casey as an agentic tool. Can you talk a little bit about what you, what you mean that? What does agentic mean to you? What does it matter to your customers, to your users?

27:48Jeff Kerr: This is a topic that's near and dear to my heart. So there are a couple different flavors of agency. One that people talk about is I think the classic definition of an AI system that receives some starting point guidance from a user or a quest. Maybe look at my case, figure out what the five next actions I should perform are, or help me add to the timeline. something that requires it to do research, work on things, and then get back to you. The system is agentic if it has a series of tools that it can operate and react to the output of, and then possibly operate in a different way and keep working and iterating and going through this loop that is not necessarily restricted in any way and then get back to you.

28:51Jeff Kerr: So if you have that, you're agentic. People also talk about agency in the sense of giving AI the ability to perform consequential actions. We draw a line currently. We don't let our AI do that. We know that some companies are letting their AI do things like make phone calls, send outgoing things, send things out. I don't know whether it's an email to your opposing counsel, file things. That to us is not really safe given the current limitations on AI risks of prompt injection. So we hold back a little bit there. Our systems are fully agentic in the first sense, but not in the second sense.

29:44LawNext Host: So they're agentic up to the point of delivering something to the lawyer, but then it's up to the lawyer to do something with that.

29:50Jeff Kerr: That's right. Another way you could put it is that our agentic AI is still read only. It helps you do things. The way that it helps, though, is not by actually doing them, but by bundling up recommended actions so that you can complete a fairly complicated workflow with a single click.

30:13LawNext Host: So other than sort of automating some of what the lawyer might have done manually before in terms of identifying facts, finding facts, adding them to the chronology, Are there other capabilities that AI brings to CaseFleet that hadn't been available in CaseFleet back in the classic days?

30:35Jeff Kerr: Yeah, definitely. Another one of the big ones is drafting. And we added this to CaseFleet a number of months ago, and it's been an extremely popular feature. so it's great to have a chronology but sometimes what you need is a letter or a draft of emotion or an email and the AI is very very good at doing things like that I think a lot of people out there are using AI whether to proofread a document to get started on something maybe create an outline and then you fill in parts of it and so we have added that functionality and case fleet and given it an extremely robust citation engine. Citations are, I love that people are talking so much about citations these days because it's something we've been talking about for 11 years now.

31:33Jeff Kerr: It's a core part of our data model. It's something we have thought about to no end. And our document review functionality and document processing functionality gives us a very deep implementation of how citations work. And so our drafting tool has certain guardrails that it has to work within that constrain how it's able to cite and force its citations to be accurate. And so, you know, I haven't tested every single AI tool on the market, but the drafting inside of CaseFleet is very cutting edge and very powerful and constantly surprising me. Yeah.

32:14LawNext Host: And by citations, you're talking about references to the documents that support the fact.

32:20Jeff Kerr: Exactly. Any assertion in a draft created by CaseFleet is factual in nature that can be proved or supported by some reference in the documents that you've uploaded. It's instructed to create structured citations that actually identify not just the page that something came on, but the exact text that was on that page. And we have non-AI code that runs over all drafts that the agent creates and knocks out any citations that are not, you know, an exact match to the underlying document text. Yeah.

33:00LawNext Host: What about just in terms of, I don't know, case analysis, case strategy? You know, does a tool like KC maybe help you see connections in cases that you might not otherwise have seen or directions to take a case that perhaps might not have been obvious just from the bare chronology or something like that?

33:19Jeff Kerr: Yeah, absolutely. And even pre-AI and case fleet, we always felt that, in a way, perspiration was the mother of inspiration because you've got your case very well organized. And all of a sudden, you see some connection that was sitting there in front of you all along. But until you have the chronology, you may not have noticed it. And the AI accelerates that process. We also use a technique called semantic indexing. so if you're looking for something in a document you swear you read it somewhere or you thought it would have been great if i could i know someone said something like this at some point in this collection of emails or deposition transcripts the ai can search using um semantic indexing which means it's not vulnerable to the fact that maybe this person didn't use the exact keywords that you're thinking of.

34:17Jeff Kerr: Maybe they just happen to use different terms. Semantic indexing sort of hits on the meaning and not so much the literal text. Right, right.

34:30LawNext Host: You alluded earlier to the fact that you, if I heard you right, that you may be sort of also getting back more into the e-discovery direction. Did I hear you right on that? And what does that mean? or what can you tell me about that?

34:46Jeff Kerr: Yeah, so if you had to make a Venn diagram for what eDiscovery is and then you made a Venn diagram of what CaseFleet does, we almost fill the eDiscovery circle with what we currently do in the software. You can upload a very large number of different types of files to CaseFleet and there are specialized document reviewer interfaces for videos or audio files, spreadsheets, deposition transcripts. So we've gotten very good at document processing and metadata extraction. Also for a number of years, we have enabled people, if they receive a document production in an eDiscovery matter, and it's got the single page TIFF files and a load file, we can ingest those types of document productions into CaseFleet.

35:44Jeff Kerr: and starting in the last month, you can now create document productions in CaseFleet. So there's a handful of features that still remain to be implemented before we truly market ourselves as being an e-discovery product, but we're extremely close and expect that to be done within the next year.

36:05LawNext Host: Yeah, I mean, what about review and tagging? Are people using CaseFleet to do that? That's part of the e-discovery?

36:11Jeff Kerr: What we hear from a lot of our customers who have access to the industrial size e-discovery tools such as Relativity is that the minute they have a smaller case, they'll just do the review in casefully because the interface is so much easier to use and simpler. Also, the e-discovery tools in a way leave them hanging because all you're doing is tagging. you're not actually building the chronology. So you're not mapping out how you're going to use each of those documents when you're getting a trial. So you kind of have to redo the work again once you finish your initial review and the other tools.

36:56Jeff Kerr: Yeah.

36:56LawNext Host: So it would be more for smaller litigation matters, not the big industrial cases, as you say.

37:03Jeff Kerr: Yeah, we're not really planning to be the destination that you would use if you have terabytes. of data. There's not a hard limit on it, but, you know, I think for those kinds of projects, someone will probably continue to use their relativity or ever long.

37:19LawNext Host: Yeah. Yeah. You've been in this business for over a decade now, and something I've commented on a lot, and I'm sure you've probably observed as well, is that I feel like the landscape for litigation-related technology has changed quite a bit over the last decade, and in particular over the last couple of years, in my opinion, driven largely by AI in that a number of companies have started up to try and serve the litigation market with AI-driven platforms, you know, even up Supio, some of those kinds of companies out there. What's your take on that? How do you you think, are you seeing the market for litigation related technology evolving, changing?

38:12LawNext Host: And where do you fit into that market? If so, I think it's an exciting time to be alive.

38:17Jeff Kerr: We're certainly having a lot of fun. I think software is getting better and better. You know, it's interesting at our company, we always have a list of things that you kind of want to do when you have time. And increasingly, you can just do those things because AI speeds up the software development process to such a degree. And so I see it being very good for everyone in general. Lawyers are going to have access to a broader range of better tools than they ever had before.

38:50LawNext Host: Yeah. So a rising tide lifts all ships or whatever the saying is in that sense. I mean, does it feel more competitive to you? Are more people kind of, I mean, like I was saying earlier, you know, a lot of companies are now talking about the fact that they do chronologies. And that's, you know, an area where, you know, at one point, there was you and CaseMap, but I'm not even sure who else was out there doing that kind of thing.

39:17Jeff Kerr: Oh, it's definitely fiercely competitive right now. I think a number of months ago, I decided to do a little survey of all of the companies that are offering AI litigation technology. And I looked at 20 of them and then just had to stop. And most of these businesses were founded in the last 30 years. Yeah. So it's interesting for sure. we love the fact that we if I could go back I'm glad that we started the company in 2015 and really got to kind of earn our our spot in the market like during this period where there was not AI and you're just focusing on these core workflows and the stuff that we built before AI arrived and ended up being very useful in the AI context which has been nice yeah yeah what about

40:09LawNext Host: even just the sort of non-litigation or non-litigation specific technology companies out there? I mean, the Harvey's and whatever's of the world, or even, you know, the frontier models. As Anthropic or OpenAI begin to push more into the legal market, they could eventually, or maybe they already have, I don't even know, build tools to do some of this kind of stuff. Are you worried about that? Do you think about it? You know, we definitely think about it.

40:40Jeff Kerr: There is certainly a benefit competitively to doing this very specialized thing that no matter how you frame it, it involves a bunch of very kind of customized user interface components for facts. and it would seem to be a little out of someone like Anthropics core competency to build something like as specialized as what we do. But, you know, at the same time, advances in the models that these labs create almost immediately have downstream benefits for users of Casely. when the Fable model from Anthropic, it was released and then it was unreleased for a couple of weeks and then it came back. We turn it off.

41:33Jeff Kerr: So you actually have transparency into the models that you're using at CaseFleet. And so you can say, I want Fable for this task. And it's pretty exciting to be able to offer that. Yeah.

41:46LawNext Host: Have you guys ever raised financing or what's your, what's the? We've been profitable since 2018.

41:55Jeff Kerr: We're probably going to be doing that in the next year. Growth has been pretty astonishing this year. It's been really quite exciting. Our team has grown a lot, but we just want to keep doubling down on what we're doing here. And I think that financing could be a good way of doing that.

42:14LawNext Host: That's great. So you haven't, up until now, it's all bootstrapped. or...

42:19Jeff Kerr: Yeah, I mean, there's been some friends and family money to get the thing started, but we haven't had to infuse the end capital for a while. Yeah.

42:29LawNext Host: Well, I always have to end an interview with like some kind of future-looking question or a crystal ball question, and I'm just kind of curious what you think. I mean, given the change within this sector just in the last two years, as you mentioned just for CaseFleet, there's been a lot of changes just in the last year. How does this play out over the next couple of years? What are you anticipating? What does CaseFleet look like in a couple of years down the road? What does litigation tech look like in a couple of years down the road?

43:04Jeff Kerr: My thesis is that lawyers are going to be fine and I think that it's going to be even more rewarding to practice law by taking a lot of the grunt work out of the practice. And my dream when I was practicing would have been to have the best proofreader in the world to look at my stuff before I filed it. I would walk around the hallways of my office with the printed out brief and I'd read it out loud and sort of throw the pages on the floor once I got through them because I'm just not good at catching typos unless I'm reading the written page. I'll read the same type of 10 times and not see it. And so I just kind of wish I could go back and practice with all of this cool technology.

43:55Jeff Kerr: And, you know, from how it works for our company, I mean, it's been good so far. I think it will continue to be so. We believe in this theory that it's not like we're going to give all of the good jobs to AI and there's not going to be anything left for anyone else to do. It's going to hopefully grow the economy in all kinds of different and exciting ways. And I hope it'll be good. I feel like it will be. All right.

44:27LawNext Host: Anything else that you would like listeners, viewers to know about CaseFleet that we haven't talked about?

44:34Jeff Kerr: We're big believers in ethical and secure AI. and we try to develop these types of tools in a very responsible way and to give people access to, you know, the great power of generative AI, but in a safe way.

44:55LawNext Host: Well, Jeff, congratulations on all you've built and accomplished here. And it's been great to catch up, not having seen you for a number of years. So thanks for doing this. Yeah, great to catch up, Bob.

45:10LawNext Host: That's it for today's episode. I hope you enjoyed it. If you'd like to share your own thoughts or comments, please do so by messaging us on LinkedIn or other social media, or just email me directly, ambroji at gmail.com. If you're a fan of the show, leave us a review. Law Next is a production of Law Next Media. I'm your host, Bob Ambroji. Please join us again next time for another episode of Law Next.

45:39Thank you.

From the publisher

Chronologies have become one of legal tech's hottest categories, with a wave of AI startups promising to turn a messy evidentiary record into a structured timeline in minutes. Jeff Kerr and his company Casefleet were more than a decade ahead of the pack.

Kerr finished law school in 2010 and made what he calls the crazy decision to start a law firm as his first job after graduating. Running an employment practice, he found that winning cases came down to knowing the chronology cold. But the only tools for building one were a Word document and a lot of patience. So he taught himself to code, left practice in 2015, and founded Casefleet.

 

On this episode of LawNext, Kerr joins host Bob Ambrogi to discuss what a decade of building fact-management software looks like now that AI has arrived. Last month, Casefleet launched Casey, a conversational AI agent that proposes facts, links them to legal issues, and drafts documents — with a citation engine that rejects any citation not matching the exact text of the underlying document.

 

Kerr deliberately draws a hard line on what he will let his AI do. Casefleet's agent is fully agentic in the sense of researching and iterating on its own, he says, but it stays read-only – it will not send emails, make calls, or file anything.

 

Among the other topics they cover:

 

  • Why Casefleet's pre-AI data model turned out to be the right foundation for AI, and why classic Casefleet still runs alongside Casey.

  • The company's move back toward e-discovery, including newly added document production, and why Kerr isn't chasing terabyte-scale cases.

  • What happens to specialized litigation tools if the frontier AI labs push further into legal.

  • Why Casefleet, profitable since 2018 and largely bootstrapped, may raise outside capital in the coming year.

 

Thank You To Our Sponsors

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  • Paradigm, home to the practice management platforms PracticePanther, Bill4Time, MerusCase and LollyLaw; the e-payments platform Headnote; and the legal accounting software TrustBooks.

  • Briefpoint, eliminating routine discovery response and request drafting tasks so you can focus on drafting what matters (or just make it home for dinner).

  • CosmoLex, helping law firms manage their entire practice in one platform, from intake to payment. Try it free.

  • Ajax, the AI timekeeper lawyers want to use.

 

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