Using AI to Improve ...

Using AI to Improve the Briefing Process | Jacqueline Schafer

June 17, 2021 | by D. Todd Smith

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If the COVID-19 pandemic taught attorneys anything, it’s that technology can change the practice of law and maximize efficiency in ways we never thought possible. But, even before the pandemic, lawyers and innovators were looking at how technology can benefit legal practice. In this week’s episode, Todd Smith and Jody Sanders visit with Jacqueline Schafer, founder and CEO of Clearbrief, about how her company has combined artificial-intelligence technology with brief writing to help both the lawyers drafting motions and appellate briefs and the courts reading them. Clearbrief is accessible in Microsoft Word, and it automatically analyzes a document’s text against the factual and legal sources cited to test the document’s accuracy. Jacqueline shares her vision of making Clearbrief so easy to use that even lawyers who don’t like technology will feel comfortable with it. Join us for a discussion of the benefits and implications that incorporating AI technology into your practice may have.

We have with us Jacqueline Schafer from Seattle, Washington. Why don’t you tell our audience a little bit about yourself, your background, and maybe your early law practice experience?

I am an attorney. I’ve been practicing for many years. I’m originally from the East Coast. I started as a litigator at Paul Weiss, a great place to learn incredible attention to detail that has stuck with me for my entire career. I moved to Alaska with my husband. It’s an exciting place to continue my legal career. I spent most of my career in public service as an Assistant Attorney General. In Alaska, I was in the appellate section and had the chance to regularly brief and argue appeals before the Alaska Supreme Court, write Attorney General opinions, and worked on some interesting issues around the state’s relationship with tribes and child welfare cases.

I joined the Washington Attorney General’s office where I was still doing appellate work, but I was advising the headquarters of the Child Welfare Agency, which is a massive statewide agency. As the appellate lawyer, you’re getting the facts and you’re getting the cases in a neat little package. You don’t see the messy stuff that’s happening earlier on in the case and experiencing in real time what’s happening on the ground. That was fascinating. It was interesting to do that while also handling appeals because it helped me in my appellate practice and gave me a newfound appreciation for the trial courts and doing complex litigation.

I got more interested in the systems aspect of why is there such a massive Child Welfare caseload? I joined a national nonprofit headquartered in Seattle called Casey Family Programs. At Casey, the goal is to try to transform the child welfare system. In that role I was in-house Counse,l but I was working with a group called the judicial engagement team across the country that was trying to help judges understand the outcomes of the child welfare system to help influence how they thought about their rulings and their cases.

As part of that, I was learning about court technology and data. I got super into data. I started writing this law review article. It was like A Beautiful Mind taking notes and like, “Yes, I want to share my thoughts on how data science and technology could improve our Child Welfare across the country.” I was working on this at night and on weekends and getting out my creative energies. Finally, I published a law review article in December 2020 in the University of Illinois Journal of Law, Tech and Policy. It was called “Harnessing AI for Struggling Families.” In writing about data science, I learned all about the underlying technology and that’s ultimately what led me to found Clearbrief. I was taking that scientific knowledge and combining it with my real-world experiences.

I’ve talked before about one particular pro bono case that I worked on where I was representing a woman and her young son from Honduras. There was this very powerful moment at the final hearing where if we lost, they would be sent back to Honduras and probably murdered. I could tell going in that the judge was not super inclined to agree with my legal theory on the case and grant asylum. There was that moment that I’d experienced so many times as an appellate litigator where I pointed the judge to a sentence in a piece of the brief where I was talking about the evidence in the case.

AI technology
 AI Briefing: There has to be a better way to use the power of tech and data science to surface those pieces of evidence and show it in context.

The judge was looking at the therapists’ reports. I saw the judge change his mind really because he saw that evidence in the context of our legal arguments. We won and he granted asylum. It was such a powerful moment. It was all of those experiences swirling around where I was thinking there has to be a better way to use the power of tech and data science to surface those important pieces of evidence and show it in context. That’s what being an appellate litigator taught me so much. It’s all about having to weave in your legal argument, but you have to show the source. You have to show the case or the factual document.

Did you have any background in AI? Your article mentions natural language. Did you have a tech background before you started digging into this?

I didn’t. I’ve always been that person though at the office who thought it was fun whenever we were introduced to the new product. I don’t know if you have this experience but there’s always a lot of groaning with lawyers when we have a new timekeeping tool or a new practice management tool. I was always like, “This is awesome. I can’t wait. This needs to be more efficient.” I’ve always been a tech enthusiast but I didn’t consider it part of my identity. It’s always something as lawyers where we have a strong identity. Being a lawyer for so many of us and being technical can seem at odds with that.

I didn’t embrace it until I started writing that law review article, and it reminded me a lot of when I got a new case. I worked on all different types of appeals and cases. I had to learn the subject matter every time, as we all do. I encourage lawyers to embrace that curiosity and learn about tech even though it can seem so off-putting and like it’s a world that’s at odds with what we do, day in and day out. It turned out to be a rewarding part of studying and I got into it by ordering some books on Amazon. That was the quickest way. I was like, “I want to learn about blockchain.” I’ll order some books and read them and slowly absorb them.

What was your undergrad major?

I was an English and French major.

There you go. All you moms and dads out there who worry about their kids with Arts and Sciences majors. Jackie not only did what we might expect, which is to go to law school, but she has turned it into a genuine interest and has become an authority, writing a law review article about AI and how you can use technology to drill down and get at what the record says and make writing more credible. 

Jackie, can you give a high-level explanation when you’re talking about AI in the legal space? What exactly do you mean by that?

I was thinking about that because I was an English and French major. I feel like I’ve found my people when I talk to natural language processing experts. They are all about language. It’s a subset of AI that is so relevant to so much of legal tech, which is analyzing the patterns in language. Some of the patterns we don’t even realize and are not something we consciously think about as writers but more like statistical relationships between words. I love the folks on my team. Kristy Hollingshead, she’s an NLP PhD on our team. We like to nerd out over the language.

I feel like that’s a great subset of AI that if you’re interested in it, start learning about that. There are so many different aspects of AI. Another relevant area has to do with image recognition. We’ve seen a lot of the products that have come out of that. That’s more what we see as consumers. The Google Image tools, I don’t know if you’ve ever been on a walk and you can take a picture now of a flower. Google can tell you what flower it is. It’s using AI to match those images. There are different subsets of AI but the one that we’re focused on at Clearbrief is called Natural Language Processing.

I’m glad that you asked that question because it is helpful to me to understand what we’re talking about in terms of what AI is. We hear the word artificial intelligence used, the naysayers are saying that AI is going to take over the practice of law, we’re not going to need lawyers anymore. In our line of work, in appellate practice, there’s not as much rumbling about that because there is an art. It’s not just data that you’re moving around on a page.

It’s absurd. Honestly, that fear has been so overblown. That’s simply not where we are with the science that we can replace human understanding, especially with writing and the complex writing that we see in briefs and motions. The human brain is so amazing. It’s hard to replicate how all of the subtle inferences we’re making about the implications of specific words. Technology is not going to replace that anytime soon. What I am interested in and what my law review article is about is the boring stuff.

I am interested in the boring, unsexy aspects of AI, which is AI to lift the administrative burden that takes away from our creativity. That’s what I argue in my law review article as well. Talking about the highest and best use of AI is not to try to determine who’s going to commit child abuse. I don’t think that’s where we’re at with the science. What we should be doing is trying to reduce the repetitive stressful tasks that take up social workers’ time, that take up attorneys’ time, and courts’ time so that they can focus on the people and, in the end, the families that they’re trying to serve. That gets less attention because it’s less interesting sounding but I think it’s interesting.

This makes me think of, let’s see, Inception is one. Let’s go way back to Minority Report. It’s comforting to hear that someone like you, who has taken a deep dive into this and dare say has developed an expertise in this, does not fear that appellate lawyers are going to be cast aside for AI tools. That’s good to hear. Let’s make it clear for our readers. Your interest in AI and your desire to lift the administrative burden, it seems like, had a strong influence on your founding of this company that you’ve identified which is Clearbrief. Can you tell us a little bit about the company and what it does?

Definitely. The vision that I had was to create a tool that doesn’t intimidate lawyers who don’t like technology and who don’t want to have to learn a whole new way of doing things. I want to build something that would fit into what we’re already doing, that doesn’t require expensive integration with any existing systems. It’s a tool that fits into your Microsoft Word process. In the high 90s, percentage-wise, of attorneys, judges, everyone working on legal briefs uses Microsoft Word. The reason is that it’s the best tool out there for all the complex formatting that you need to have in legal documents.

We’ve built Clearbrief, it exists in two places. The first is that it’s an add-in for Microsoft Word. Whatever it is you’re writing or working on, just click one button and Clearbrief pops up. The workflow is that you can upload right in Microsoft Word, our happy place. You can upload any factual documents that you’re talking about in your brief. The record on appeal, the transcripts, any orders in the case or other things, drag them in as PDFs. You don’t have to drag in the law.

You click a button and Clearbrief automatically hooks up all of your citations in your document. It can identify in your draft every place where you’re talking about a citation and hook it up to the source document so that it’s displaying it for you on the right-hand side of Word. As you’re writing and editing, you can see the source. I wanted to create a place that was a real workspace that covers all of those tasks that we have to do like the administrative burden piece.

man frustrated with hands on head
 AI Briefing: We should be trying to reduce the repetitive, stressful tasks that take up so much time to focus on the people we’re serving.

One thing that has always stressed me out is the table of authorities. It’s the worst piece of the process for me because you’re editing, and you’re writing, and you have to wait until the very end to finalize the table of authorities. I’ve talked with over 200 attorneys, judges, and paralegals across the country in all different practice areas. Nobody knows how to do a table of authorities with the tools in Microsoft Word. Attorneys don’t know. Most of them are relying on paralegals to do it, but then it creates this traffic jam at the last minute where you want to be editing things, but you can’t move things around because then it’s going to take time.

Clearbrief is a one-click table of authorities without you having to tag things as you’re writing and say, “This is a cite, this is the id.” You don’t do any of that, just one click. That’s a pretty magical moment when I show Clearbrief to folks. Part two is that, when you’re done, you would just download your brief as a PDF and file it in the normal way, but you can also click a button that we call judge view. What judge view is doing is taking all of that data from your brief and sending it to your secure account in the cloud. You can view the brief alongside the source. Your brief is completely interactive for the judge. You could share the link with the judge, and with opposing counsel as your courtesy copy via email.

They can access this version of your brief that judges love. You made the judge’s life 1,000 times easier. They don’t have to have Clearbrief. They don’t have to have anything special. They can just click and look at it in this fully interactive way so that they can see the record sources and the legal sources. We’re using publicly available legal data including the opinions, the statutes, the regulations, everything. You don’t have to have a subscription to any specific legal research tool. Anyone who has the link can look at the source documents. I want to also come back and share more about how the AI piece fits in. I didn’t cover that yet but that’s the workflow.

That sounds like our version of hyperlinking but on steroids. In Texas, Jackie, our courts are pretty sophisticated when it comes to electronic documents and we’re told to do it right. We need to be hyperlinking our PDFs. Some people will go so far as to link outside documents like their Westlaw or Lexus cite or they’ll provide all the documents in one PDF, which sounds like that’s something like what Clearbrief does. They’ll hyperlink within to get where we’re going. It sounds like Clearbrief is a tool that puts all that together. As you say, click it and forget it more or less.

That is similar to other state appellate courts like New York that do require certain hyperlinks. The processes that lawyers have gone through to achieve that is an expensive time-consuming process. It’s very manual. It’s printing off a case and saving it as a PDF and then having to hyperlink each thing manually. This is simple and instant. We’re identifying everything, pulling in the source for you. The other piece that I wanted to highlight that I didn’t cover yet is during that cite checking process.

When you have your draft in Word and you have the source documents, Clearbrief is scoring the writing for you. It’s looking at the sentence that precedes the citation. It’s looking at whatever source you cited. You can open your opponent’s brief right there in Word. It’s scoring it for you to see like, “The source document doesn’t support what they’re arguing.” It flags it in red. It can suggest other places in the factual record that seem relevant to what you’re talking about.

This is a different way to write your facts section. Imagine you’re writing your facts. You’ve already read the entire record. As a human lawyer, how else would you know what to write about? You can go through that creative process of writing out the facts and telling that story. After each sentence, you could put ER one, Excerpt Record one, however you’re referring to the record. Clearbrief knows, “Let’s find a record cite to support every single thing in here.” It can link it up for you. Many of us have a habit of saying to our associates like, “Go find the cite for this.” This can speed up that process.

You hit right on the question that I intended to ask you. Many of us know you’ve got it in your head what you want to say and say in your facts section, that’s a great example. You’ll start writing and you don’t have that record right at your fingertips at that moment. I see it done all the time. I frequently do it this way where I’ll put the word cite in a bracket. There shouldn’t be any brackets in my brief when it’s done. That is amazing to think that a tool like that could help fill in that citation without me or the paralegal or associate, whoever has to go back and locate the specific page in the record. That’s fantastic.

It’s quite magical but it’s not doing it for you. You still have to go and look at it and compare and see. Plenty of times, I’ve written something in my free writing mode and from my memory. I go back to the record and I’m like, “Wait, no. They never said that. That didn’t happen.” Clearbrief can tell what you’re talking about and then suggest, “This seems like this would be the best match for what you’re trying to say.” It gives you that feedback to say, “I better go back and double-check that.” It is coming back to your creative process but it’s taking that boring part of going and finding something and looking through that PDF, and opening that PDF. It’s taking away that boring part.

We see a lot of similar products in the market to what Clearbrief does. I don’t know that I’ve ever heard of something that does quite what you’re describing. You mentioned scoring the writing. Is that score limited to the accuracy of the citations? Do you go beyond that into writing style or something? What comes to mind, for example, would be WordRake or maybe a BriefCatch in terms of actual writing style? Is there a feature like that?

We are focusing on the accuracy of the substance. That’s where I saw this opportunity to innovate because there is no other legal tech product that’s doing all of these things for you, applying AI in this way. It’s confirmed by famed Legal Technologist Bob Ambrogi in his piece on Clearbrief. He said, “This does something that no other legal tech product does.” For that idea about highlighting writing style tips, I see the potential for that in the future. One of our investors is Professor Bryan Garner, a famed Texas Lawyer, Scholar. His legal writing style tips have been so influential to me personally throughout my career. I didn’t know him before reaching out to him and explaining the concept for Clearbrief pretty early on actually and he was excited about that. He understood the need for folks to be paying attention to the accuracy of the writing.

I see the potential at some point to add in writing style tips as well as writing organization tips. What I’m excited about is how we’re seeing our early users use Clearbrief. You can not only use it for those finished or near-finished drafts but you can also use it early on in the outlining process as you’re trying to write out a sentence and idea. “John had the gun in the car,” or something and Clearbrief can find all those places in the record that mentioned John, whether it’s having a pistol in the automobile. It doesn’t have to be the exact keywords that you’re using. It can suggest the most relevant places in the record that relate to the concept. That can help you as you’re outlining to see what is in the record, how do I tell this story in a way that’s going to support my legal theory? That’s something I’m excited about as we see and hear the feedback from our early users.

If you upload the record, it’ll test your writing against the record for accuracy. You’ve mentioned access to publicly available versions of case law. Will it test your accuracy and representations of case law as well?

That’s right. We are not offering the same suggestions like we are for the factual documents and citations, but it will give you feedback on whether it says what you’re claiming it says on this page of the opinion. That is also almost a writing style tip in a way. I had the honor of talking to so many amazing litigators while I was doing what they call customer discovery as you’re building the product. The best fanciest litigators in the country would tell me, “What I consider good writing is writing that if you go to the source, it pretty much says 100% what the source says. You shouldn’t be adding a lot of embellishment. There shouldn’t be all sorts of fancy adjectives or your wild take on it. It should be one-to-one pretty much. That’s good legal writing.” It’s hard as someone who is a former English major. It was one of the hardest things for me when I went to law school to take away all my flowery adjectives. You want it to be crisp, clear, and you establish trust with the judge and with the reader when they see that, “That’s exactly what the court held here.”

AI technology
 AI Briefing: Your brief is completely interactive, so you can share the link with your judge and with the opposing counsel, and they can access this really cool version of your brief.

I see as an offshoot, listening to you talk, this has tremendous potential to allow access to justice in places where it didn’t exist before because you’re efficient. You’re adding so much efficiency to attorney time and I guess you talked about child welfare. That seems like a great place where you have underrepresented litigants on the civil side that this thing can shortcut the cost of representation in a meaningful way.

That’s what I hope for because it’s very difficult. You’re seeing massive growth in the number of self-represented litigants because people can’t afford an attorney for child custody cases, for family law cases. There are massive consequences to generations of families because of that. If we can make it a little bit easier on attorneys to get the briefs in the right format so that it’s crisp, it’s clear, they have cited the facts. That was an interesting thing I learned too. In some practice areas, especially in the trial court, attorneys are not following the gold standard that we consider important in appellate law of having a citation after every fact that you’re referring to. That’s hurting the outcome of the case because they don’t have the resources to go and find that information in the record and clarify it for the judge.

It does bring an interesting phenomenon that I realized in talking to so many judges specifically. We don’t all have the chance to talk to judges about things. Except we go to these CLEs. We hear the big picture. I heard the same thing from all the judges I talked to. They get super frustrated when they go to look up whatever you’re claiming that the record says if it doesn’t say that, or if you took them to the wrong page, or if you’re sloppy with your citations. They will put down your brief and they will go to your opponent’s brief. They all said that. They’re like, “I’ll put it down. It’s not worth it. I don’t trust that attorney anymore.” They lost credibility. I don’t think I ever realized fully honestly as a practitioner how important it is. We don’t always think about what the judge is doing with our writing when they get it.

We’ve talked about the appellate side of things but on the trial side, in particular, where you don’t necessarily have a record or a staff attorney, something like a summary judgment where you can link all your source documents together. Provide that to the trial judge who probably doesn’t have the time and resources to delve through it quite like a Court of Appeals judge and staff attorneys might, it seems like there’s a lot of potential impacts there to shortcut that side of the process for them.

That’s why I wanted to build something that wasn’t a tool for the lawyers. It’s really with that judge view feature I was talking about. It’s a systems tool because we are doing all this work on our side to find the right documents to make sure they say what we’re claiming they say. We’re making the judge, we’re making their clerk, we’re making their paralegal, and we’re also making opposing counsel. Maybe we don’t care about opposing counsel but it is frustrating. I feel like we should maybe care about opposing counsel because if we wrote an awesome brief and our law is airtight, our facts are airtight, I want to show that off to them. We shouldn’t be making everybody replicate the same work. Let’s make that easy so that we’re all on the same page. Let’s get to the heart of the dispute.

What does this tool do? Is it an efficiency tool that has the potential to remove a lot of friction from the process? We’ve been mired in inefficiency and friction throughout the development of our profession. I’m thinking back to my early days as an appellate lawyer in a very large firm and we had a paralegal who was dedicated to cite checking our briefs and, of course, this also takes me back to thinking about law school and law review stuff. 

It seems like this tool has the ability if you use it properly and do it in conjunction with a good draft to begin with. You apply the tool and it would eliminate some of the need to have other humans look at your work to verify its accuracy because you can see what the software has flagged for you. You go look at it yourself and the software is hinting to you this passage may not support what you’re saying in your brief. You can judge for yourself whether that’s accurate and not rely on another person to tell you. Have you seen a use case for that, are the law reviews contacting you and saying, “What do we have to do to get licensed for this?”

Yes, we’ve had enormous interest from law professors to use Clearbrief as a teaching tool but I want to mention one other feature that I didn’t talk about. We are still finalizing it and it will be available shortly. Clearbrief can automatically fix all of the formatting of your citations as well. You don’t have to manually go through and review every little suggestion about the formatting, it will fix it for you. If you want to dig in and see what was fixed, you can. It’s very efficient because we are using natural language processing and an AI-driven approach. It’s different from the rule-based approaches that currently exist in terms of fixing formatting of citations.

That’s a feature that law reviews are very excited about. To your point about whether it replaces humans. It is going to allow for doing more with less, but one of the things that we’ve done differently maybe than other legal tech companies is that from the very beginning, I focused on paralegal stakeholders. I interviewed a lot of paralegals and we partnered with the National Paralegal Association, NALA, because paralegals are important to the entire process. The other dynamic here is that in general, I found with talking with folks, they’re not billing for the approximately eight hours per brief that they’re spending on things like cleaning up the formatting of the cites and cite-checking. They’re generally writing off about that much time because they’re like, “I spent too much time in the brief or I’ll write that off.” They might feel like, “That’s overhead and I’m going to write it off.”

If firms can gain efficiency there, they can use that time for work that’s billable, that they’re billing for. That’s valuable to the business. From the paralegal’s perspective, the paralegal’s time can be freed up to do more organization for the firm. To do more high-value tasks that allow small firms to earn more money, like there’s data about how the faster you respond to inquiries, to new clients, the more likely you are to get more business and to become profitable. It’s helping paralegals view themselves as project managers. They’re not so bogged down that they have to build a table of authorities manually.

It seems like it frees up some flexibility and attorney fee schedules and things as well. If you’re working on a flat fee type of arrangement, it makes a lot more sense to have this tool so that you don’t have to spend eight hours going back and doing that thing when all that’s going to do is cut into the amount of profit you’re going to make off your flat fee at the end of the day.

Exactly. I haven’t seen so much resistance to people thinking, “I’m going to make less money if I use this tool.” It’s apparent that this efficiency will enable you to earn more money and do the work that’s more visible to your clients. I’ve been thinking about this judge view feature where you share the interactive version of the brief. It doesn’t give any of that semantic analysis or the scoring. It is a fully interactive version. I feel like sharing that with your clients would give them a better understanding of the value of the appellate work that you’ve done. I don’t think they always realize like, “I wove together a brilliant narrative.”

There’s something to that because depending on the type of client, we’re dealing with the trial lawyers more often than the actual clients but you’re right. When you get the bill and it’s all this time for writing a brief, and researching, and checking citations, all that stuff, it is nice to have a bundled-up package of this is why we have to do that. Here’s what the record looks like, here’s how it all fits together in the end. That does make some sense. 

When it comes to alternative fee structures, think about flat fees as an example. That’s how flat fee-based lawyers become more profitable – by becoming more efficient. This is a ginormous efficiency tool potentially. There’s a lot of other technology tools that help make us more efficient. It seems to me that if you can spend a little less time digging around in the record and a little less time poking holes in every little citation in your opponent’s brief because you’ve got a tool where you’re almost at second base as opposed to taking off after hitting your base hit. That is tremendous in terms of the efficiency that you can gain. The more efficient you are, whether it’s a flat fee or hourly fee, the more profitable work you can do. 

I’m not a sports expert. I’m a musician. But I get what you’re saying.

Efficiency is the name of the game. Clients expect it, we need to be removing the friction as I said and not doing things that wind up being wasted time. It sounds to me that Clearbrief is a product that helps advance the ball on that, to complete the sports analogy.

Child Custody blocks with family graphic
 AI Briefing: You’re seeing massive growth in the number of self-represented litigants because people can’t afford an attorney for child custody cases and family law cases.

Another thing that I’m curious about is being able to share your published filed briefs via the judge view feature on your website and to showcase some of your best briefs in a way that a client could understand. It would help to explain, “Why me? Why are you hiring me instead of this other attorney down the block? Look at the craft of my writing. Look at this brilliant piece that I wrote.” That’s another thing I’m interested in exploring.

I love that idea too because one way that we used to do that in the old days was we had paper copies of our briefs and we would send our client a duplicate of what the court got. When you can hold it in your hand and turn the pages, you can sense there’s some amount of craftsmanship that goes into this. It’s much less so in the case of electronic briefs. What you’re suggesting, Jackie, is you can show value in other ways that’s not outward craftsmanship. Not the quality of the paper, or the quality of the cover of the brief, but you can see how we’ve had to link things up in certain ways that a layperson isn’t equipped to do. That’s a great point.

Few people outside of the parties’ attorneys and the court will ever look at the record. To have that combined and public-facing makes a lot of sense because you can read a brief. Unless you’re going to go and dig into what’s available, you have to take the brief at face value. If you’re seeing it also paired with some of the key documents, the record testimony, that kind of stuff does make a richer reading experience to understand all that went into, “Here’s what we’ve taken from this cold record and turned it into something readable and understandable and persuasive.”

I’m interested as well in talking with courts. We’re talking with several state appellate courts about having them publish their opinions with Clearbrief so that the public can also understand that. I don’t know if you’ve had this experience but as a trained lawyer, when I read appellate opinions sometimes, I’m like, “I cannot follow this.” I’m having to look up everything that they’re saying to follow what they’re talking about. It’s one small step towards a more accessible justice system if the public could read, “What case are they talking about? Why does this case stand for this idea that they’re talking about here?”

It’s been very cool to run Clearbrief on US Supreme Court briefs because the judicial appendix is available. I was looking at a brief that was about a property dispute or environmental dispute. When they’re talking about the tracts of land, with Clearbrief you can see the images while you’re reading about it. You can see what they’re talking about. That’s a cool feature of Clearbrief. It can identify the images that are in the record. It’s very powerful, particularly when I’ve looked at criminal briefs and other things to be able to see the pictures of the evidence, to see the scene of the crime. It makes it a richer interactive experience for the person who’s trying to make the decision.

We had a criminal judge on and he was talking about how they put a case opinion out that involved a video. They put screencaps of the video in the opinion and then put a hyperlink and hosted the video on the court’s website so that people could go straight to it and see the video as they read the opinion. It sounds like you’re shortcutting a step there. You don’t have to have the court play host to all of that. 

How does an English and French major who educated herself on artificial intelligence turn this idea into reality? You mentioned a team early on in the conversation. You’ve got folks around who know how to code this stuff?

I’m happy to break that down. It does have some Texas connections there. When I was thinking about this idea, it was great being here in Seattle because everybody is a technologist. I started by talking with a friend of a friend who was an AI engineering developer. We went to the courthouse library. I showed him examples of opinions and case law and I was like, “Could this work? Is this data structured enough that it would work?” That was my very first inspiration when he said, “Yeah. Your idea makes sense.”

To hear that from an engineer gave me the boost I needed to keep going. Via LinkedIn, I was looking for other women who had experience in building AI products. I connected with Anne Jude Hunt who’s one of my advisors. She’s the VP of product at She has a technical background and has built several AI products. She’s based in Austin, Texas. That’s the Texas connection there. Anne was so excited. Coming from someone who had done that hard work of taking an idea and turning it into a real product that works, to talk with her and strategize with her was invaluable.

She ended up connecting me with a developer who helped me build the early prototype of the algorithm. I was doing my customer discovery, talking with so many lawyers. The idea shifted and changed as I talked to so many people and heard patterns about what their biggest pain points were. It resonated with my own experience. From all those folks I interviewed, I got briefs and records and we started testing it. It was a manual process at first in testing algorithms but that helped me gain enough traction so that I could go out and build the company.

Some of the other big breaks that happened were through LinkedIn and networking. I connected with Mark Britton, who was the founder of Avvo. He has since exited. He is a famous investor here in Seattle. He was an early believer in Clearbrief and understood how this was novel and how what we’re doing could change the entire system. He was one of my earliest advisors along with Brian Garner. I started to get critical mass there, which helped me with fundraising. I was able to hire my full-time technical team, which includes my fabulous CTO, Jose Saura, who, after twenty years at Microsoft building AI products and leading teams of engineers, left Microsoft and joined Clearbrief.

He’s been essential in taking the algorithm and this idea and productizing it and turning it into a real working awesome product. I have to shout out to my husband, who is our lead front-end engineer. He’s working harder than anyone because he has to listen to me complain and stress about it. I mentioned Kristy Hollingshead and we have several other fantastic NLP engineers and contractors and full-time employees who have gotten Clearbrief to the product that it is now.

AI technology
 AI Briefing: AI can lead to much greater efficiency within the system so that courts are moving faster and their decisions are fairer.

Did this mean Jackie that you’re no longer actively practicing law? Sounds like this is not a garage-based business, if it ever was, anymore.

I am still keeping my head in the game because I do pro bono work for some Seattle nonprofits. That’s how I keep up my knowledge of the appellate practice. My main pro bono work for the last several years has been working on appellate briefs with Legal Voice, which is a Northwest Women’s Rights and LGBTQ Rights Organization. I’ve done several appellate briefs with them and continue to consult on different litigation matters.

You have certainly given us a lot of insight and good information. We appreciate you being here. I wanted to ask you a broad question based on your work. Being a practicing lawyer and digging into AI, what is your vision of how AI can fit together with the broader legal system?

My vision is that not only will we use AI for the things that it’s good for, which are primarily the stressful administrative tasks that take away from our satisfaction as lawyers, but this will lead to much greater efficiency within the system so that courts are moving faster and their decisions are more fair. Ultimately, we all have more satisfaction in our work as attorneys and the justice system can serve the public in a better way.

You’re hitting on something important because of every little step that we take in Texas and a lot of places in the US, we have completely transformed the practice of law in 2020. Perhaps not willingly but we’re seeing the effects of that. It’s been tremendous. We were talking to a judge who’s a family court judge and she said, “In 2020, I have started to see people in my court that I never saw before. By doing Zoom, I’m able to serve a whole group of people that were never here before.” In these types of solutions, you do start to see what we weren’t doing correctly the last time around. It’s great that these solutions are out there continuing to pick up those holes and cracks and fill those in and find new ways to make sure that the system works for everybody.

This is a moment in time that’s so unique where the legal profession is embracing change. I’m ready to seize that moment. I hope everyone is too. We’re all thinking about what’s important in our lives. We should be using our work hours for the most rewarding work, and that benefits our clients the most. That benefits the justice system the most. Tech is a big piece of that. It’s not the only piece but it’s exciting to see that transformation happen.

We always ask our guests if they have a tip or a war story that they’d like to offer our readers. Do you have anything you’d like to share? 

It’s a war story and a tip. What I learned from watching the video was that you don’t realize what your superpowers are as an appellate attorney. It helped me realize the importance of being able to find that specific fact in that moment of pressure so that you can get in the details. We know the details and we care about the boring things that can end up unlocking the whole case. I saw that play out when I watched the video where a justice would be asking me a question. I pored over that record and I pored over the details of the cases. I had a thoughtful answer about how this one detail should change the outcome of the case. If it’s possible to get a recording of yourself doing the oral arguments, that can help you appreciate what’s strongest and what’s weakest about your appellate practice. To remember that our ability to focus on those boring, mundane details is a superpower, we should be proud of that. Thank you so much for having me. This was fun. It’s wonderful to talk with other people who think about these things.

We appreciate it. This has been so interesting. It’s great to hear that people like you are out there thinking about this in the legal space and finding ways to improve both the process and the results, frankly.

The legal technology nerd in me is grateful because I enjoy hearing about this stuff and getting a vision of where things might be headed in the future. Thank you, Jackie, for being with us. 

Thank you so much.

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About Jacqueline Schafer

Jacqueline Schafer is the Founder and CEO of Clearbrief, a platform transforming how participants in the justice system write and interact with litigation documents in order to save lawyers non-billable hours and achieve better case outcomes.

Jacqueline was recognized by VentureBeat as one of four semi-finalists for the 2020 Women in AI Rising Star award for founding Clearbrief, as well as for her law review article describing how AI and natural language processing (NLP) will transform government social services.

Before joining the startup world and founding Clearbrief, Jacqueline served as Senior Director, Program Counsel for the national child welfare nonprofit Casey Family Programs. Prior to that role, she served as an Assistant Attorney General in the Washington and Alaska Attorney General’s Offices, where she specialized in appellate practice and complex litigation.

Jacqueline began her career as a litigation associate at the New York law firm of Paul, Weiss, Rifkind, Wharton & Garrison. She is a founding board member of the Washington State CASA Association, and a board member of the Seattle Repertory Jazz Orchestra. She also serves as an advisor to two AI organizations focused on social impact AI innovation, Microsoft-backed startup X4Impact and Think of Us.

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