Ep 252: How Clearbrief Helps Lawyers Find the Best Facts to Support their Writing, with Founder Jacqueline Schafer

This episode features Jacqueline Schafer, founder and CEO of Clearbrief, discussing the development and impact of her AI-powered legal tool designed to enhance legal writing by integrating evidence directly into Microsoft Word.

1. Clearbrief's AI tool enhances legal writing by integrating evidence directly into Microsoft Word.
2. The tool's development was inspired by Schafer's own experiences and challenges in legal writing.
3. Clearbrief has successfully attracted significant investment, indicating strong market confidence.
4. The product has evolved based on feedback from a diverse range of legal professionals.
5. Schafer emphasizes the importance of founder involvement in product development and customer relations.

1. Introduction to Jacqueline Schafer

Jacqueline Schafer discusses her background and the inception of Clearbrief. She highlights the recent $4 million fundraising and its implications for the company. Jacqueline Schafer: "This was sort of an opportunistic chance to build upon the success and the growth that we're seeing."

2. Challenges and Solutions in Legal Tech

Schafer talks about the challenges she faced in the legal tech space, particularly as a woman founder, and how these experiences shaped the development of Clearbrief. Jacqueline Schafer: "I've always been focused on talking about product, talking about what customers are saying, what customers want."

3. Clearbrief's Impact and Evolution

Detailed discussion on how Clearbrief assists lawyers by keeping critical evidence visible during the writing process, and its continuous evolution based on user feedback. Jacqueline Schafer: "Clear brief is a Microsoft Word add-in that helps lawyers find and then keep the evidence visible."

4. The Future of Clearbrief

Schafer outlines future plans for Clearbrief, focusing on expanding its capabilities and market reach. Jacqueline Schafer: "We are definitely evolving. There's new features that we're releasing pretty much every month."

1. Utilize AI tools like Clearbrief to enhance legal document accuracy and reliability.
2. Engage with product feedback to continuously improve usability and functionality.
3. Consider the security and integrity of legal documents when integrating new technologies.
4. Stay informed about technological advancements that can streamline legal processes.
5. Foster a diverse and inclusive environment within tech startups to encourage innovation.

Jacqueline Schafer, the founder and CEO of Clearbrief, was inspired to start the company based on her own experiences as a litigator and appellate advocate. A pivotal moment for her came in an asylum case she was handling pro bono, when her ability to point the judge to critical evidence that supported her arguments saved her client from deportation and possible death. At that moment, she later old me, the thought crystalized for her, “If you can show the judge the evidence that really tells your client’s story, that’s how you win.’”

Soon after, Schafer set to work building Clearbrief, AI-powered software that works within Microsoft Word to help lawyers find the best facts to support their legal writing. This week, the four-year-old company announced that it had raised an additional funding round of $4 million, bringing its total funding to nearly $8 million. Along the way, it has racked up numerous awards, including Legalweek’s 2023 litigation product of the year, Clio’s 2022 Launch//Code Developer Contest, Legalweek’s 2022 new law company of the year, and the American Legal Technology Awards’ 2021 legal tech startup of the year.

Schafer is our guest today on LawNext, as she shares her journey from practicing lawyer to startup founder, describes how Clearbrief helps lawyers in their legal writing, and discusses what this latest investment means for the company and its customers.

People

Jacqueline Schafer, Bob Ambrogi

Companies

Clearbrief

Books

None

Guest Name(s):

Jacqueline Schafer

Content Warnings:

None

Jacqueline Schaefer
That has been very powerful is having, you know, big law customers who saw like, hey, like, yeah, we don't really have anything that does this. And actually we would love if it did these other things that we've always wanted in a product. And I know the traditional advice for startup founders is like, don't let your customers lead your roadmap. But it's all about, you know, curating the roadmap is how I think about it. And that's why I still stay very, very involved in talking with customers every day, because it helps me implicitly sort of know, oh yeah. What this firm is suggesting. Actually, every customer that I've talked to, they also want that. And I know they'll love this.

Bob Ambrogi
Today on LawNext, an interview with Jacqueline Schaefer, the founder and CEO of Clearbrief AI powered software that works within Microsoft Word to help lawyers find the best facts to support their legal writing.

This week, the four year old company announced that it had raised an additional funding round of $4 million, bringing its total funding to just under $8 million. Schaefer was inspired to start the company based on her own experiences as a litigator and appellate advocate. A pivotal moment for her came in an asylum case she was handling pro bono when her ability to point the judge to critical evidence saved her client from deportation and possible death.

As Schaeffer told me when I first interviewed her in 2021, I thought, if you can show the judge the evidence that really tells your client's story, that's how you win.

Today, we'll learn about Schaefer's journey from practicing lawyer to startup founder. Hear what exactly the product does to help lawyers in their legal writing, and find out what this latest investment means for the company and its customers.

This is Bob Ambrogi, and you're listening to law next, the podcast that features the innovators and entrepreneurs who are driving what's next in law.

We'll get to all of that in just a moment, but first, please take this moment to learn about the sponsors whose generosity supports this podcast.

Ditch manual billing and experience a seamless billing solution with Bill for time, the easiest to use legal practice management software, from standardized invoicing and customizable templates to built in payment processing. Bill for time as your trusted partner for streamlining your firm's time tracking and billing processes, find out more about how Bill for time can enhance your practice by visiting billfortime.com dot. That's bill fourtime.com dot.

One more ask before we get to today's episode. If you enjoy law. Next, please take a moment to leave us a review on Apple Podcasts or wherever you listen to the show.

We'd appreciate it.

Now on to today's conversation with Jackie Schaeffer.

Jacqueline Schaefer
Jackie Schaeffer, welcome to Lawnext.

Jacqueline Schaefer
Thank you so much for having me.

Jacqueline Schaefer
Bob, pleasure to talk to you. I want to get back to the beginning and the origins of clear brief, but given that you've had some news this week, I thought, let's start there, and we can kind of work our way backward in this conversation. But you've just announced a new fundraise of $4 million.

Why was it that you wanted to do this raise at this point of time, and what does it mean for a clear brief?

Jacqueline Schaefer
Yeah. So this was sort of an opportunistic chance to build upon the success and the growth that we're seeing. My goal in founding the company has never been to just continue raising massive vc capital, but to become profitable to deliver value to our customers. But this was an opportunity to work with investors that I think are fantastic and, you know, are really believe in the mission. So I may sort of do things a little bit differently than some other founders, and that I really, it's really important to me who's on my cap table. It's really important to me that, you know, we have a diverse cap table that believes in women led companies.

So these are all things where when it, you know, the opportunity arose to take in some additional capital.

Yeah, it just worked out really well. And we're now just sort of in build mode with continuing to expand, especially our sales team, to keep up with the demand.

Jacqueline Schaefer
One of the things you said in announcing this raise was that it's in part fueled by your growth in the Amlaw 200 sector. How has that growth been kind of characterized? Have you been typically small firm have been moving upmarket or what's been that sort of trajectory for you?

Jacqueline Schaefer
Yeah. So we had, you know, started out working with small firms. They were the ones, you know, back in, you know, 2020, when I launched the company in 2021, when we released our beta, you know, version of our product, who were willing and excited to work with us and to use AI. So I, you know, it's been amazing. So we continue to serve that customer base. And what we saw, though, in 2022 is we started to get a really strong pull from big law. And in order to satisfy them, we had always had the strictest security requirements. Really from day one. That was something I knew would be table stakes as a founder. But we needed to further enhance architecture, security, some of the features that are needed to support the volumes of documents and the level of collaboration that big law requires. So this was before the generative AI craze hit in 2023. So we've been really focused on serving those customers and also learning how to deploy the technology and onboard firms of that size. So we've really hit our stride in the last several months and there hasn't been, we haven't done a ton of pr about it, really. But I'm so proud, honestly, to see the largest global law firms that are using our product across their litigation departments were being used still as well, by courts, by government agencies, by in house teams, including Microsoft's legal team. I can at least share that because they have talked about it publicly.

So this is, yeah, it's just a really wonderful moment for us as a company. And it still, for me, is all about the product and the features that big law needs and wants also tend to provide a lot of benefit to different types of legal organizations, too. So it's working out well.

Jacqueline Schaefer
Yeah. I've always been kind of impressed by some of the investors that had been behind your company. I literally first spoke to you back in 2021 at the introduction of Mark Britain, the founder of Avo, who was one of your early seed investors.

And that early seed round included some pretty prominent people like Brian Garner, the author of Garner's Black's Law Dictionary, the former general counsel of Microsoft, and later came to include Jack Newton, the founder of Clio. Were you always kind of savvy about fundraising or is this something you've had.

Bob Ambrogi
To learn how to do and have you gotten better at it?

Jacqueline Schaefer
Fundraising is my least favorite part of this entire process.

I won't, you know, regurgitate what you already know, that, how difficult it is, especially for, you know, women led companies, you know, to raise capital. It's been a very punishing experience, I think also because when I founded Clear brief in 2020, it was just around the time when the fall of atrium that, you know, short lived legal tech company that had raised, you know, insane amounts of capital and VC pretty much, you know, thought legal tech was the worst investment ever after that. So that's been my, you know, initial experience. And so I knew that in order to attract investors, I needed to come to the table with credibility. I was a really a first time founder, so. But I had a, you know, a strong legal career, a decade of practice at, you know, Paul Weiss in government and in house counsel at, you know, very large institutions. So I brought, you know, I brought my own credibility too. I'll give myself some credit there. But for sure, leveraging, you know, each investor that you get to get excited about your company, and it really helps to build that momentum. But I've learned a lot in the last few years about how best to work with my investors and advisors in terms of how to use what skills they're strongest at, the connections that they have that are most beneficial to the company. And so for sure, I think I've gotten better at that piece of it. But my number one goal has always been to focus on the company and not on fundraising. So again, I'm probably different maybe than other founders in that regard.

Jacqueline Schaefer
Yeah.

Bob Ambrogi
Do you have any sense?

Jacqueline Schaefer
I mean, you mentioned that this current round of investors includes several with, you know, a record of supporting women led founders, and that's been the case all along with your investors. What's been your experience as a woman founder in the legal tech space?

Jacqueline Schaefer
Yeah, I think overall there's this tendency to sort of place women founders in a different space in some ways where we're just not given the credibility, partly.

Jacqueline Schaefer
Because they were like aliens in the space for a while. There were no women founders. There were so few women founders in legal tech for a long time.

Used to track that on a regular basis, and the list was, for a long time, very slim.

Jacqueline Schaefer
I think we're starting to see more and more female founders come into legal tech, which I hope I've had some small part in that by just being relentlessly vocal and visible, even when people, you know, I felt like were sort of leaving us out of the conversation or because we weren't, you know, focused on just talking about fundraising. And I've always been focused on talking about product, talking about, you know, what customers are saying, what customers want, and that doesn't get as much sort of attention in the legal tech world.

Also, you know, from a pretty, like.

Jacqueline Schaefer
I said, for the last attention, you mean the ability to go out there and talk about what you're doing? Is that what you mean?

Jacqueline Schaefer
Oh, no, sorry. Just focusing on product and user adoption and that sort of thing. And that's what I kind of tend to post about on LinkedIn and talk about versus talking about fundraising and talking about investor strategy, talking about models, AI models. These are all things that I think are obviously valuable and part of the legal tech conversation.

So, anyway, I've just sort of focused on what I'm most passionate about and eventually I win people over.

I think once the people who are legal tech enthusiasts start out by getting excited about those kind of seemingly sexy aspects of it, and then over time they're like, actually, I really want to understand what is the use case? How are people using it? What's their feedback? How do we get them to adopt it? Those kind of un sexy questions under the surface, that's where those questions are, the things I've always been drawn to. So does that mean we get maybe less attention in the legal tech space? I don't know. But anyway, I have heard from other female founders that I gave them some confidence to pursue their idea and pursue their vision. And also a lot of male founders. I'm constantly getting inbound DM's from founders in general, so I'm happy about that.

Jacqueline Schaefer
It's funny when you kind of talk about sort of the inside baseball aspects of the legal tech world, and then there is the rest of the legal tech world, or rather the rest of the legal world that just uses tech in their day to day work. And my experience is that people do get it pretty quickly when they see a clear brief. And I know you saw the post I just put up last week where I had spoken to a group of trial lawyers in North Carolina, and in particular, I had this judge come up to me afterward and say, I want that. I love that. But my court won't let me use anything like that. Which seemed to me a really strange thing that the court wouldn't allow that. But I've talked about clear brief. I've been in places where you talk about clear brief, and it seems like when you talk to lawyers who are out there practicing law and creating legal documents, they get it right away and are really excited about it. I think that that's partly attributable to the fact that this is really did come out of your actual experience and out of your real life story. So I said we'd get back to it. I know you've told the story a million times, but why don't you just kind of share how it is that you came to develop this in the first place? What was that?

Bob Ambrogi
There was a sort of a pivotal.

Jacqueline Schaefer
Moment, I think, that kind of had the light bulb go off in your head, right?

Jacqueline Schaefer
Absolutely. So, you know, I've been a litigator my whole career. I started out at Paul Weiss wherever. Of course, there's such an emphasis in that setting on accuracy and perfection and legal writing as a team sport, really, where everything right is gonna be scrutinized by 20 people. I then went to practice in government, where I was doing appellate work. I was regularly arguing before the state supreme court, it was amazing. I mean, I loved that so much. And it was such a different writing process where this time, it's like you have a massive caseload, and you have to write everything yourself. You can get feedback, which then you have to incorporate at the end, and there's a scramble. So I just had, you know, years and years in the trenches of writing and also caring deeply about writing and seeing. I think it really was that a palate experience that that really helped me see that. Like, wow. When I got that final opinion from the court, like, they really used my ideas in my writing. Like, you know, they. It came through. And then, you know, I had this really transformative experience.

It was, like, around 2018, where I was representing a woman and her toddler in a pro bono asylum case, and I had written, like, a 50 page brief or something like that. It was a lot. And we got to this final hearing where if we lost, they were going to be deported and in extreme danger and absolutely terrifying to feel like, oh, my God, this is resting on my advocacy. And when we got into that hearing, the judge immediately, just by verbal cues and body language, was signaling that he was super frustrated with my client. She was pregnant. He was just upset. And I felt like, we're going to lose. This is horrible. But there was a moment where I pointed him to one of the pieces of evidence that I had gathered, which was some declaration by a therapist, and the judge listened to it, heard it, and reviewed it, and I saw him change his mind, and he believed my client, and we won. And it was for sure a nail biter, because it was like, there were different, you know, arguments that we had made. And he was like, this one rejected this one. It was like the last, you know, possible legal theory and sort of like a catch all legal theory. And ultimately, it came down to his gut feeling of, you know, whether this. This woman and this family had been subjected to that extreme trauma. And it was the evidence and his interacting with it that changed his mind. It was not what I said or even what my client said, actually. So I just thought that was such a powerful moment, and it really helped me sort of visualize what I wanted to do with taking the legal writing, taking the evidence, and keeping it visible.

I was also, at the time, like, learning more about AI. I wrote a law review article about AI and how I thought it would transform the child welfare space, which I think is so cool, because it was definitely, I think it foresaw some of the things that we're seeing today.

Jacqueline Schaefer
The use of data to transform child welfare or something like that, was that I was actually looking for it. I couldn't find it.

Jacqueline Schaefer
But is it is. It's called harnessing AI for struggling families. And it's about how government agencies could be using AI to help with some of these core problems that I saw when I was an assistant attorney general advising government agencies. I sort of saw some of the structural problems.

So, anyway, I was a big nerd, essentially, is what this all boils down to. But I will say I knew when I learned more about AI and natural language processing that this was going to transform what lawyers did. And, yeah, I think that was, to me, it was an exciting time because I felt like I had this insight that other people didn't have. And I think a lot of people tend to get dejected after being rejected or having their ideas sort of sneezed at. And so I think that was a very pivotal moment of just having that conviction and moving forward to raise capital, to start a company, to build a prototype, to build a team.

Jacqueline Schaefer
That's a huge leap. I mean, how do you go from, you sort of see the power of evidence, you see that it's important to winning cases, but you're a practicing lawyer. How do you go from that point to founder and CEO?

Was there a moment when you just said, that's it, I'm quitting my day job and working on this?

Jacqueline Schaefer
Yeah, there was. I think one of the biggest factors for me really just had to do, like, it was just something that I'd always felt since I went to law school, where I knew I wanted to do something that had an impact, I wanted to give back. And at that point, I tried a number of different roles in the legal world. And at every role, I sort of felt, like, limited. Like, oh, God, I have so many ideas. And people don't always like people with big ideas in the workplace. It's just they want you to just stick to what you're, you know, your day job kind of thing, stick to what you're supposed to do. And so I'd always kind of had that feeling. So I think I was just old enough and at a point in my career where I just felt like, if I'm going to do it, I should just do it now. And I see this opportunity, I think a couple other things, which was, you know, living in Seattle, there's a lot of entrepreneurs here. And I was learning, getting more involved in that community, I felt like a fraud. So just, you know, that is for sure something, an emotion, probably every founder experiences during this time period where you go to these events and you're like filling out your name tag, you're like, founder question Mark. You're not sure what you're, what you, who you are.

Jacqueline Schaefer
Was that how you met Mark Britain? Because he's in Seattle also.

Jacqueline Schaefer
So actually, I met, I met Mark Britton very strategically where I was, you know, reaching out to different people and, you know, who knew Mark. And eventually I met certain people and it was through this person, through that person, they introed me to Mark. And yeah, when I first got that meeting with Mark, the first thing he said was, everyone always wants me to invest in legal tech. I don't do it. I'm not going to invest. So just FYI, I was like, okay.

But when I told him my ideas and my vision and I sent him a truly embarrassing pitch deck that was very poorly formatted, he kind of saw beyond it, instantly saw that, that potential. And so he was like, let's do another call. You know, he, and so over time, I think he really was such a huge influence in how I kind of got to that next step. So I got to give him props to Mark. He's. Yeah, and I just think there's been, there's been mentors like that at different stages of this journey. And Mark continues to be just an amazing sounding board, so really grateful to have him.

Bob Ambrogi
We've talked so far on this podcast about why Jackie Schaeffer founded Clearbrief and her initial journey as a founder. What we haven't talked much about is the product itself.

In the second part of the interview, we'll dive into the product and what it does.

But before we do that, please take a moment to learn about the sponsors who so generously support this podcast.

Paradigm is revolutionizing the legal industry by offering a comprehensive suite of innovative technology solutions combining the power of top tier legal practice management platforms, including practice Panther, Mariskesh, Lollylaw and Bill for time, Paradigm provides a complete suite of tools designed to meet the unique needs of law firms of all sizes and specialties. With native online payments and intuitive interfaces, Paradigm makes it easy to streamline your workflow and focus on what matters most, serving your clients.

Discover more@joinparadigm.com dot welcome back to law. Next. Just before the break, you heard Clear brief CEO Jackie Schaeffer talk about Mark Britain, the original founder of Avo, who was an early investor in an advisor to clear brief. I shall have an email mark sent me in February 2021 introducing me to Jackie, in which he wrote, quote, what they are doing is incredibly cool, and I believe it will revolutionize legal writing and advocacy. So what exactly is it they are doing? Up until now in this interview, we haven't delved into that. So as we turn to the conversation, I asked Jackie to describe just what it is the clear brief does.

Let's get back to that.

Jacqueline Schaefer
Yeah, so clear brief is a Microsoft Word add in that helps lawyers and anyone doing legal writing find and then keep the evidence visible while they're writing in word.

We do use now generative AI to generate timelines that have hyperlinks where you can see all that evidence in word while you're reviewing it and editing it. And it's really designed as this end to end platform, though. So you might start off with a chronology, but then you're turning that into a facts section, then you're turning that into a brief that needs to be site checked or a motion, and then you need to create exhibits and you need to do your table of authorities, and then you want to send a hyperlinked version to file with the court.

Clear brief stays with you through that entire process and also site checking the law, the legal sites to prevent if you've used generative AI on your legal research. We don't do the legal research portion. We're focused on the fact research. But we do check over that final product.

Right. In words. So that's the one thing that we've really continued to hear from our customers is like, wow, this is a really complete platform. And that's what I'm saying. It takes years in the game, years in the trenches with customers, listening to them, to think of all the, there's just so many kind of minute and tedious problems that are involved in getting from idea to filed motion.

Jacqueline Schaefer
But it's all about verifying and connecting those facts. I mean, you've got, somebody's working in word. You've got the word document brief or whatever you're working on in the left hand side of your screen. You've got clear brief on the right hand side of your screen, and you've uploaded documents, transcripts, exhibits, whatever else it might be. And you're able to find the facts in all of that that support what it is you are writing or to verify that, in fact, you've properly cited to the correct facts. Right.

Jacqueline Schaefer
Exactly.

Jacqueline Schaefer
Good, because that's what I said last week when I talked about it.

Jacqueline Schaefer
You got it right. So it really is solving one of the biggest issues, honestly, with work settings, where you're having to collaborate on writing, where the associate does something, they send a document to the partner, their supervisor, the client, a colleague, co counsel, and that person is reading like essentially a flat piece of paper if they don't have clear brief. So they worry like, okay, you're telling me this is what the evidence said? You're telling me this is what the case said. If I want to investigate that, I have to go look it up. And truly we're all so busy, unless you make it super easy for people to see and check things that can fall by the wayside. So this is what we hear all the time from like, the partners and big law and everywhere that they love that they can easily check their associates draft and they don't worry, I'm signing my name to this. Did this person secretly use chat GPT? And I'm going to be on the front page now for hallucinating everything in my brief. Like, they don't have to worry, they see it in clear brief. So we also have several features that are very, like, patented, very unique to our tool that, you know, are very popular, like the add fact site button.

So this is something that, like, I thought of basically when I was, you know, a big law associate where as an associate, you might send a draft to the partner and they add a bunch of stuff in there and they put add Factsight, add factsite, and they send it back to you and you're like, where did you get this? I don't know if this is true. And there's 50,000 pieces of evidence.

Well, you can easily import and dump all that evidence into clear brief. We integrate with relativity, imanage, netdocs, clio, mycase, and now I can search through and find, I can select that sentence and the AI will suggest this page could prove that, this page could prove that. And I can just insert a hyperlinked citation. So I hope that was like an oral description of the software.

Jacqueline Schaefer
Well, no, it does help to see it, actually.

And anybody listening to this, I think you can hop onto YouTube or onto the clear brief site and see. Well, actually, I know on your site you've got a bunch of demos up there that show it all visually and it's very helpful to see. But it is the kind of thing where, like I said, I demoed a bunch of products last week, and the one that stuck in this judge's mind was clear, brieftainous, and she wasn't the only one who mentioned it to me afterward at this conference. So.

Jacqueline Schaefer
Put me in touch with them, I'll help them get it.

Bob Ambrogi
Well, I think part of the problem.

Jacqueline Schaefer
Sometimes with a lot of, especially in this age of genera, a lot of the stuff that's coming out is people have difficulty, I think, sometimes seeing how it fits within their law practice, within their workflow. And this is just so obvious. And it's also unique. I mean, I was trying to think of who your competitors are. And, I mean, there are certainly other products out there that kind of help with brief formatting and citing and cleaning up and editing text and that sort of thing. But you don't really have a direct competitor in terms of what you do.

Jacqueline Schaefer
We don't, and that's what we hear all the time from customers, which is we looked at all these other generative AI tools. We decided to go with clear brief after, you know, our users said this one really was useful.

And also, this is literally giving us the full spectrum of what we're doing with a document. There's so many tools now that can just generate something for you, but they haven't thought through. Okay, well, how am I getting the evidence in? How am I, what's the architecture to ensure security?

What about all this extraneous data that's in the margin or whatever of the document? What about when I want to share it with these people? There's just so many little things that are needed. So I would just say that has been, I think, very powerful is having big law customers who saw, hey, yeah, we don't really have anything that does this. And actually, we would love if it did these other things that we've always wanted in a product. And I know the traditional advice for startup founders is don't let your customers lead your roadmap, but it's all about, you know, curating the roadmap is how I think about it. And that's why I still stay very, very involved in talking with customers every day, because it helps me implicitly sort of know, oh, yeah. What this firm is suggesting. Actually, every customer that I've talked to, they also want that, and I know they'll love this.

So it helps me figure out how we can continue to offer that unique value.

It's really just about like listening.

Jacqueline Schaefer
So keep doing that.

Jacqueline Schaefer
Maybe that's, keep doing that.

Jacqueline Schaefer
That's important for the CEO to keep talking to the customers. I think some of these, some of these founders get too big for their britches.

So you officially launched it back in March of 2021. How has the product evolved since then?

Jacqueline Schaefer
Yeah, so we had, yeah, initially really just focused on displaying citations to the law, displaying citations to the facts. When you analyze a document, and there's just so many iterations, for example, of how people might cite to different things. And we actually, we have four issued patents that cover sort of that journey. We went on to figure out, how do you build a tool that's very flexible at detecting? They meant this to be a reference to the deposition, but they just spelled everything wrong. And it's a weird citation. It doesn't look like a citation. So we've put a lot of development time into citations. Again, not a sexy area in 2021, I think it's gotten more exciting to people. Now we're in the age of. We really can't trust anything anymore. We've got to see, we've got to verify. You better show us where you got this. So making that a reality is that's. We've put a lot of focus on that. Then we added more around expanding our integration so that we could seamlessly bring in the factual documents.

In 2023, we launched our generative AI tools. That has been huge. Those are now some of our most.

Jacqueline Schaefer
Popular features, which are the timeline and the chronology.

Jacqueline Schaefer
Is that. Yeah. And then you can turn your timeline or your search results into a narrative with citations into a demand letter, with citations into an investigation report. So our product is different than a lot of AI tools, where it's not choose your own adventure.

It's not like, do anything you want with clear reef. It's really not. It's like, we know that you want to do these specific things, and so we've put a lot of work into making sure that will go smoothly for you. So I think that it's also sort of like a product choice there. Um, which, you know, I think it is really exciting, you know, to, when you use generative AI to feel like, wow, I can ask it anything I can. But when I think about my own experiences using very open ended prompting generative AI tools, I don't end up using the output very frequently. It's fun to do, but it's not. So that's where I think we really have staying power compared to maybe some other generative AI tools that are saying, look at, people are using it. People are using it. Well, they're typing stuff in the search bar, in the prompting bar. But are they actually filing that with the court? Are they actually sharing that with the client? So once you sort of get into the details of talking with customers, another really cool thing is that from very early on, customers have been putting their, you know, have been using clear brief on real work. So versus just saying, oh, we can only use publicly available, you know, documents. They're using it on real assignments that, and they're filing it, the hyperlinked versions with the court.

So, yeah, we're battle tested in that way.

Jacqueline Schaefer
Yeah. And worth noting, I forget whether you mentioned this earlier, is that you can use it not only to check your own work, but to check your opponent's work. If you get a brief in from an opponent full of citations to the record or whatever else, you can check the accuracy of those.

Jacqueline Schaefer
Right, exactly. And there's nothing more fun than using that add fact site. You're like, okay, you put a bunch of stuff, but you didn't put any citations.

I'm going to find what else is in the record that contradicts what you wrote. So that's always really a fun way to use AI.

Jacqueline Schaefer
Yeah. So given the product evolution to date and some of the features that you've added in some of your listening to your clients in terms of what they're looking for, does it continue to evolve or have you had a kind of a stable product at this point? What are your plans and thinking about the product going forward from here?

Jacqueline Schaefer
Oh, yeah, we are definitely evolving. There's new features that we're releasing pretty much every month that are enhancements that are directly the result of our conversations with customers.

I don't want to say too, too much because I do feel like that's kind of our competitive advantage right now, is that we have a lot of customers and we listen to them. So, you know, and I'm starting to notice, like, I think when I see new startups popping up every day, I'm like, oh, there's our website copy, there's my newsletter copy. And so it has made me a little more guarded. I think that's kind of an interesting, like I said, we've done what we've achieved on far less capital than most of our competitors.

And I think it's really because we've listened to our customers and we have moved quickly to implement new, new features, and we're always innovating.

And that extends to innovating and how we train people, how we, the security architecture options that we offer, we're really not just standing by and standing by the sidelines.

Jacqueline Schaefer
Clearly, there are the investors that you announced this week, and your prior investors, see opportunities here for growth.

Where are those opportunities for growth? Are they primarily in expanding your market? Are they also in adding new types of products to what you're already doing? Where do you see that happening?

Jacqueline Schaefer
Yeah, it's really just about sort of doubling down on what we've been doing and we're just seeing really rapid adoption. I think there was just sort of a turning point with, with big law where they realize like, oh, wow, everyone is using it. Like, we need to use it too. And also getting it in the hands of their users. You're like, oh, this has been much more thought through than other things we've tried to give litigators. So this is the time to double down on growing our sales team. We recently hired an awesome vp of sales, Corey wise, and we just are continuing to, you know, expand that.

We still need to hire sort of like a head of marketing. A lot of our marketing has been organic. We haven't done paid ads. It's really been organic. You know, word of mouth and podcasts like these.

Jacqueline Schaefer
I mean, do you have, I was actually wondering is, do you have marketing and pr people or are you kind of, are you kind of the marketing person?

Jacqueline Schaefer
I've been the marketing person. We do have, you know, some folks helping me now, which is amazing. But yeah, I still, I have a very high bar for content. Like I said, I try to use chat GPT, but I have my own voice that I think our customers really relate to. So, yeah, no, again, I do something, for example, I send an update email to our customer base exploring the new features, showing them how I'm using it and how they can use it.

It's not written by anyone else, it's written by me.

And I think that's what there's people like that, they really respond to that. And I get, you know, so many wonderful messages saying, like, oh my God, this just saved me today when I own my brief. Thanks for making this video. And, yeah, I love it.

Jacqueline Schaefer
Well, you're, you're kind of a shy person anyway, right? You know, you don't, you're not very comfortable on stage or.

No, you were, you were a jazz vocalist as well. And I mean, I, sorry that I talk about this every time I see you, but still, one of the most memorable times for me of seeing you was during Startup Alley in 2022 when you were one of the companies pitching there and you got up and sang your pitch and it was, it was fantastic and it captivated everybody in the room. And that was the first and last time anybody sang their pitch at Startup Valley that I can remember.

Jacqueline Schaefer
Well, I do think it's important to really, you know, stand out when you do pitch competitions.

And just in general, people want to feel like they trust and know their legal technology companies. I think that is an important part of our brand that we've built is being interested in my journey and like, who is this crazy woman?

Jacqueline Schaefer
I think the fact that you have a genuine story of what the problem was that you encountered, how you saw this as being one that other lawyers had and then turning that into a product again, I think that's why people relate to it. It's clearly something that is a common problem and this is the only solution to it out there that really does it in the way that you do it. So that's a good thing.

Just totally unrelatedly, somebody was asking me just this earlier this week as somebody in a startup about should I hire a pr firm? Should I hire a marketing firm? I don't really know that you should.

I debate that a lot, but I think probably a lot of it is how comfortable you are with that sort of thing as a startup founder. But founders who are one on one with people and genuine and passionate about their product do a lot more to convey that message than any PR person is ever going to do, I think.

Jacqueline Schaefer
Well, honestly, I think it also comes with being involved in interacting with customers because I've gotten so much more comfortable talking about the product than I was just from. I'm every day, all day doing that. So it will naturally, I think, make you better at PR by just talking with customers.

Jacqueline Schaefer
Back when I first talked to you in 2021, I actually also still have the notes from that conversation. I was looking back at those, and one of the things you said to me at the time was you had to learn pretty quickly how to lead a tech company.

That was three years ago.

What more have you learned about how to lead a tech company? Or what kind of advice would you give to others who were maybe where you were three years ago?

Jacqueline Schaefer
Oh my gosh, that is a really hard question. I feel like the learnings are just coming constantly, every day. And I mean, basically so much has been having a mentor of my CTO, Jose Saura, who he leads our technology team, and he was at Microsoft for 20 plus years, leading AI teams, building AI products. And so he just, yeah. Has such a great way of really respecting what I bring to the product conversations and my ideas that I have from reading all the time about different models, different ways, different ideas and strategies we could incorporate, and also being realistic with me about what we should focus on and the bandwidth of the team and that sort of thing. So I think that's probably the number one thing, is just having a partner, technology partner, who you can really rely on and trust to help you grow and develop because you have to get more technical.

And so that's something that, it's just a muscle that I'm always growing is maybe it's similar to what we do as lawyers, too. When we get a client and they're sort of a new area of law, we're like, what is, what does that acronym mean? And you're just constantly having to up your game and educate yourself so that you can communicate with the engineering team. I'm also, yeah, really excited about, I think, let's see, what else have I learned? I think that trusting my own sort of taste, because it's not just taste, product tastes and product sense that's been developed at random, it's because I am, like I said, I'm in customer calls, trainings, onboardings, one on one conversations with partners, one on one conversations with law firm, GCS, you know, in house counsel. I'm just like, in all these conversations and it's feeding my algorithm of my brain.

So I just think again, I know I've already said this, but, yeah, just being a part of those conversations, never get too busy to be a part of those conversations because that's what hones your product sense of where the roadmap should be going. And so much of it is just like a gut feeling. And then one last thing, which is, I think, don't discount your artistic sensibility in leading a tech company, because tech is, yes, it's very numbers based and math based, but the success of products really often come down to like, did we delight somebody? Did we make it feel easy for them? Did we sort of show them a new way of doing things? And so recently, I'm super excited. Hired a fantastic, you know, she's an experienced designer, basically, and user, you know, head of user experience to help me continue to ensure that using the product feels really intuitive, feels like a delight.

And, yeah, I think that's. It's just you should like. One of the things that I really appreciated about her name is also Jackie. Shout out to other jackies is her artistic sensibility and that this is really an art. It's not always a science, like leading a tech company. So I don't know.

Jacqueline Schaefer
I'm sure you want clear brief to make lots of money, and I'm sure your investors want clear brief to make lots of money. But are there other kind of metrics for success that you look at as you kind of look ahead to the future of this company?

Jacqueline Schaefer
Yeah, I mean, I want to leave the legal profession a healthier place that's really what I'm going for. I think that a lot of the dysfunction that we see in legal workplaces and the stress and the sadness that a lot of lawyers feel is because they're sort of alone in dealing with and solving very tedious, complicated problems.

Yes, I know everybody says I want them to focus less on the, you know, the drudgery and more on the high level lawyering.

It's really, though, if we can help them understand that from the beginning of working on something, you can set this up for success so you won't be crying in a bathroom stall at midnight, you know, before the brief is due. It will set them up to interact better with their colleagues. It will set them up to communicate better with the judge. It will set them up to win. And ultimately, I think, set everybody in that, that case up, because litigation is about this adversarial system, where, in my personal experience, really, the only thing that sort of shortcuts the adversarial nature of it is the facts. And, you know, if you're ever in an argument, the one thing that, that sort of shuts down the argument is like, well, let's, let's both look at this, this email together. Let's both look at this document, and let's get on the same page about what we're arguing about. Let's get on the same page about what's reasonable.

And, yeah, we disagree, but if we can all at least make it easy for us to look at the evidence, I think we can resolve things, you know, in a better way that's healthier for the legal profession and has better outcomes for clients.

Jacqueline Schaefer
If only that were true and other aspects of our lives, it would be great.

Unfortunately, facts seem to care, not carry the weight they once did.

Jacqueline Schaefer
We need an add fact site button for social media.

Jacqueline Schaefer
Me, too.

I like that clear brief for social media.

Well, before we wrap up, was there anything else that you wanted to say about clear brief or about the latest news or anything else?

Jacqueline Schaefer
Yeah, I mean, really, I'm just excited. I think that, I wish I could say more about how our customers are using it. We just are, really. We have such exciting stories that we hear every day.

We can't talk about it because our customers don't want everybody knowing their business, which I get.

But it brings me so much pride on behalf of my team to see what lawyers and legal staff and in house counsel what they're achieving. Judges, clerks with our tool and hearing their user stories, I think, is what should give everybody a lot of confidence that AI and legal tech are really having a positive impact on our profession. And it's not just hype. There is a reality to it. And hopefully we'll start to hear more of those user stories publicly.

Jacqueline Schaefer
All right, my last off topic aside is to say I was again, in researching this, I came across your swing 49 bandcamp page. I think, is that your group? I assume that's not a thing anymore, or is that. That's not your.

Jacqueline Schaefer
When you realize.

I just. Yeah, we did a performance, like, I think, was it last month or do a performance every couple months. And, yeah, that's. That's what our album, maybe that was one of the things that. That helped me get my head around, subconsciously around the idea of starting my own company was, you know, recording an album is also something that nobody asks you to do. That it's like you have to put a lot of blood, sweat and tears. There's a couple of my original songs on there, so. Yeah, check it out.

Jacqueline Schaefer
Yeah, I did. I was listening to it this morning. Gypsy jazz from Jackie Shafer.

Jacqueline Schaefer
Yeah. Oh, yeah. One of my favorite songs in there is, hey, muse. Gotta check out that one. It's about, can you be inspired by something other than heartbreak?

Jacqueline Schaefer
Well, Jackie, thanks so much. I really appreciate your coming on the show, and it's been a real pleasure to talk to.

Bob Ambrogi
Always good to see you.

Jacqueline Schaefer
Thank you so much. Really appreciate your interviewing me.

Bob Ambrogi
My sincere thanks to Jackie Schaeffer for joining me today to talk about clear, brief, and congratulations to her and everyone there on the recent fundraise.

I hope you enjoyed the conversation. If you'd like to share your own thoughts or comments on today's show, please do so by messaging us on LinkedIn or, or X or by emailing me directly ambrogiomail.com dot.

If you're a fan of Lonnx, please leave us a review wherever you get your podcasts.

Lonex is a production of Lawnx Media. I'm your host, Bob Ambrogi. I hope you'll join us again next time for another episode of Law. Next.