CEO Roundtable With Ari Kaplan: Legal industry CEOs reflect on vibrant 2024, look ahead to 2025
Ari Kaplan talks with his 2024 CEO roundtable.
Ari Kaplan recently spoke with the following CEOs in his annual Ari Kaplan Advisors CEO roundtable about the opportunities of 2024 and the expectations for an industry in perpetual change in 2025.
- Katherine Allen, Flo Recruit
- Dru Armstrong, AffiniPay
- Jon Canty, Sandline Global
- David Gruskin, Legalpeople
- Rick Hellers, Scan Logic
- Greg Hong, Steno
- Katya Linossi, ClearPeople
- John Marshall, Airia
- Alaa Pasha, Maptician
- Jackie Schafer, Clearbrief
- Andre Wouansi, Accurate Legal Billing
Ari Kaplan: As you know, I am an analyst who covers legal. I create content that connects companies to their clients, serving as a conduit between buyers and sellers. I have the privilege of connecting leaders, and my objective with this initiative is to introduce you to each other. Please describe your background and your organization.
Katherine Allen: I’m the CEO of Flo Recruit. We make recruiting software primarily for law firms with over 100 attorneys. The NLJ 500 is our sweet spot; we work with over half of the Am Law 100. We think there’s a huge opportunity in talent.
Dru Armstrong: I’m the CEO of AffiniPay. We’re the parent company of MyCase, LawPay, Casepeer and Docketwise. We provide software-embedded payments and fintech to lawyers. We work with 70,000-plus law firms and process over a $15 billion run rate in legal services fees. I am proud of the work that we did with the legal market in 2024 and expect to do in 2025.
Jon Canty: I’m the CEO of Sandline Global, a digital evidence consultancy that deals with e-discovery forensics, project management, hosting and review.
David Gruskin: I’m the CEO of Legalpeople. Technically, the organization is called LegalPartners Group, and we have two brands, Legalpeople and the Partners Group. We are a legal talent provider with four service lines: managed document review, primarily in the e-discovery space, flexible attorney staffing, contracts analysis solutions and direct hiring.
Rick Hellers: I’m the CEO of Scan Logic. We simplify law firm finances, and we’re solving the e-billing crisis. During the first half of my career, I was the CFO of large law firms and have been a serial entrepreneur throughout the second half for the last 20-plus years.
Greg Hong: I’m the CEO of Steno, a court reporting agency. What makes us different is that we offer deferred payment options for cost-conscious clients who take cases on contingency or worry about writing off costs or chasing clients for payment. Over the last couple of years, we have built technology to allow attorneys to take depositions more thoughtfully. This includes a Zoom app that allows attorneys to share documents during a deposition and our most recent release, Transcript Genius, which enables attorneys to interrogate their transcripts following a deposition.
Katya Linossi: I’m the CEO of ClearPeople, developer of the Atlas Intelligent Knowledge Platform. Atlas is an all-in-one platform for Microsoft 365 that ensures quick access to expert information for lawyers and their clients. Atlas is used by a range of law firms, from boutiques to the Am Law 100. It specifically transforms knowledge management by auto-tagging and unifying content from Microsoft 365 and other repositories into a centralized AI-powered platform.
John Marshall: I’m the CEO of Airia, which has developed an AI orchestration platform that allows our end customers to build and deploy agents quickly. We help organizations that want to deploy an enterprise AI solution do so with their data, keep it safe within all of the compliance regulatory requirements, and build AI solutions.
Alaa Pasha: I’m the CEO of Maptician, a workplace management solution that empowers companies, primarily law firms, to navigate changes to the modern, flexible workplace. Our platform helps facilitate space optimization, bringing people together and creating a collaborative environment.
Jackie Schafer: I’m the CEO of Clearbrief, a Microsoft Word add-in and platform that helps lawyers, judges and paralegals read and review writing in Microsoft Word. They can see the evidence, especially with generative AI, which will create hyperlinked timelines and deposition summaries, assigning a hyperlinked citation to every sentence, allowing the reader to examine the evidence instantly. It also helps you get the document filed, reducing tedious administrative tasks associated with filing in court. Clearbrief is used across the Am Law 200 by the most significant global law firms, courts, government agencies and in-house teams, like Microsoft.
Andre Wouansi: I’m the CEO of Accurate Legal Billing. I have been in the legal space for a little over two decades and have worked for insurance companies for the better part of that time. I used to own an e-billing company, and about eight years ago, I decided to start the first AI-powered OCG compliance company. Today, we have offices in New York, Pittsburgh, South Carolina, London and Asia.
Ari Kaplan. (Photo by Tori Soper)
Ari Kaplan: Where did you find opportunities in 2024?
Rick Hellers: When I first entered legal tech, our systems were time, billing, accounting, word processing, fax machines and photocopiers. Twenty-five years ago, our choices were still extremely limited. There were 10 vendors and about 10 solutions. They served our needs, and they’ve evolved substantially since then. What’s incredible about the legal tech industry now is the amount of energy, investment and choices. There is overwhelmingly powerful technology for the business and practice of law, which is exciting to see.
Alaa Pasha: Two years ago, I decided that legal as an industry would be a great place for us. As you recall, many companies were unsure what to do post-pandemic. Everyone was going to close offices and send people home. Then some decided to force everyone back in or fire them. We saw real maturity within the legal space because part of the culture in the profession is being in the office and mentoring and training people to become the next generation of lawyers. As we reflect two years later, we’ve made tremendous progress within the top 500 law firms and are tweaking our solution to fit their needs better. We’re very proud of evolving with the state of work and leveraging legal tech to create a collaborative environment. We make it easy for professionals to come into work, collaborate and find their friends. We made a bet on this industry, and it has been an absolute delight for us.
David Gruskin: Reflecting on 2024, it was a once-in-a-generation year for the buzz about technology on the horizon. However, we decided to double, triple down on humans because that is our core expertise. We’re bravely being boring, and for better or worse, there’s a lot of excitement in the space around us, so we’ve decided to stick to our guns.
Dru Armstrong: When I went to law school, if you had told me I would end up in legal tech and it would be the focus of the Y Combinator graduating class, I would have laughed. But I’m constantly reminded in conversations with our clients of our mission to educate, so we focus on empowering each firm’s financial management and financial wellness. If you think about ’24 and then look ahead to risks in ’25, we fall too much in love with the technology and lose sight of the core business and practice of law challenges. We don’t do enough to bring our actual clients along and make it really simple and accessible to them. As technology gets buzzier and buzzier, our clients have a real thirst to be part of the conversation and to be educated by learning from each other.
Katya Linossi: Everyone’s been in love with the idea of AI and trying it out, but my biggest reflection is that there is now an understanding that effective knowledge management is more essential than ever, which presents an opportunity for us to educate the market about the value of data and knowledge. People are starting to see that knowledge is the AI sweet spot.
Andre Wouansi: I have noticed that law firm executives lack data about their business, which limits their ability to build and improve relationships with their clients. They only engage in discussing fees, which is a one-way relationship. You must provide some data at the table with an insurance company executive to have a meaningful conversation. Data allows you to have meaningful conversations and build relationships with clients. I want to educate CFOs, COOs and managing partners of law firms about how to use information to drive growth.
Ari Kaplan: What are you most concerned about for 2025?
Katherine Allen: For our clients and maybe BigLaw firms in general, it’s very hard to get in the door, but once you’re in the door, they want to buy more from you. It sounds like a champagne problem and exciting, but it’s opportunity indigestion. There are so many things that they would love to have, so we have to make really hard decisions about what we build. One of my biggest fears for 2025 is that we don’t move fast enough to keep up with the market demands and the changing legal talent landscape.
Dru Armstrong: We have a strong macro lens on the strength of the legal economy, and there will be a lot of uncertainty for 2025. This is a concern because the ability to unlock value by adopting technology and investing in it is predicated on a healthy, growing legal market. We see more business being highly indexed to interest rates, and given the lack of clarity about next year, I continue to worry about us sticking a soft landing. We take for granted that we are the largest and healthiest economy in the world, and that the ability to expand legal technology and support services really depends on lawyers continuing to grow their practices and invest more in their operations. People think the legal industry is recession-proof. It is recession-resilient, especially when you blend all the different practice areas and look at our market’s B-to-C and B-to-B components.
Jackie Schafer: That actually makes me excited as a product that focuses on litigators because they tend to do well regardless of the macroeconomic circumstances. I’m most concerned about the number of generative AI products coming out and saturating the market. Law firm customers seem overwhelmed. My thesis is that the product users [who] are trained on first and fully incorporated into their workflows will win. So we have a very strong strategy for building the adoption of Clearbrief’s generative AI tools in Microsoft Word with embedded responsible AI. It comes down to understanding the personas of the legal industry and how they think about their work. Our familiarity with the psychology of the profession helps us train faster than our competitors.
Rick Hellers: We need to accelerate the value of legal tech. There are hundreds of solutions available, and they’re all really good. Law firms want to deploy and see value quickly. So every decision and product we make, every customer interaction and every potential customer interaction are designed to prove to them that we can accelerate their value with our solution.
Greg Hong: We focus on maintaining differentiation with our AI-driven products when OpenAI and Anthropic are dumping gobs of money into their platforms. We are never going to invest Fortune 10-type company dollars into development, and there are a ton of great solutions out there, some featuring AI. I don’t know how much of this is sustainable over a long period, so we have an internal bias towards professional services and showing attorneys how to use the products themselves. As a services company in the court reporting space, we have built some unique technology for our industry. But if I take a step back, I’m not sure how much of that lead we’ll be able to maintain over time, as token limits expand as the UI layers OpenAI and others add to their products. I don’t know if our differentiators today will be relevant five years from now or if we can build tools that someone far larger than us doesn’t also build. We are asking ourselves how we maintain that lead over time.
Jon Canty: In digital evidence and computer forensics, the data landscape is becoming more complex than off-the-shelf solutions can manage, so a gap is widening. I consider this an opportunity because many legacy platforms were developed for a simpler data environment. The opportunity all comes back to service, which is what we provide. The more hype there is around AI, the more it feels like service is neglected, even though AI will not save us. So I’m bullish on 2025 regarding the people aspect.
Ari Kaplan: What skills are in the highest demand for your team or the legal industry overall?
Katya Linossi: Dev ops resources are in high demand, as we add more complex features, like Microsoft 365 Multi-Geo support. I read a 2024 annual job skills report that cited AI, cybersecurity and data ethics as the top emergent skills for 2025. This is what we’re hearing from our customers. We especially hear more about AI coming into roles both internally and externally.
Alaa Pasha: Engineers are always in high demand, but the most critical role for us is that of customer consultants who can help guide the customer. We work with firms with 2,000 people, and where they are located and how they work there is very important. As we continue to grow, I’m challenging each of our teams to be a consultant to the customer. We don’t want to be shy when talking to an Am Law 30 firm because we have worked on a given project 200 times, and this is their first, so we have stronger and more helpful experience. Before entering the legal tech sector, I spent most of my career in the hospitality industry at restaurants and hotels, where the culture is to guide and consult the client, not just write down and execute tasks. AI skills will be a huge differentiator for everyone. We need to educate and scale our teams to ensure they do not complete something in 45 minutes that will take AI seconds to complete.
Rick Hellers: With the rapid advancement of legal tech, we are all in the process of reinventing ourselves. We should change how we look at data; operate our businesses; think about challenges; and interact with humans, organizations and machines. And it’s daunting, so I’m listening more to the younger generation, trying to understand how they think, and soliciting a broader range of feedback. The challenge is to reinvent ourselves as leaders and, more importantly, help those around us reinvent themselves.
Ari Kaplan: How has your leadership style changed?
Katherine Allen: Our company now has about 40 people, which feels very different from when it was 10. We have a mixture of executives who have been there and done that, as well as early employees who joined us straight out of college and have built a ton of knowledge inside the business. So mixing those two is a challenge.
Ari Kaplan: Where do you see the legal market headed in 2025?
John Marshall: I probably have 25 different lawyers that I use across my businesses and personal life, so as a consumer of services, I want my interaction with my lawyers to be more efficient. I want them to use their skill sets better and receive the full value from what they’re doing. I want them to move nonvalue-added tasks to AI. I want to empower our clients and employees to do everything in half the time with a third of the resources, so my job as a leader is to question everything we’re doing and ask why we are doing it instead of technology. That’s a leadership question. That’s a personal journey question. That’s a really important question for everybody as we build our companies. We’re all going to be facing competition from the hyperscalers with infinite money and infinite resources, so I think about whether we are moving fast enough. I want to push all of the people servicing me to be AI first. Of course, to do that, they will have to consume services from the CEOs on this call.
Dru Armstrong: There will be two big trends: continued proliferation of solutions powered by generative AI and data-centric cloud platforms. We will continue to see more froth on the Gartner hype cycle as we’re in the hype zone. Then there will be platform consolidation. Many established companies raised capital this year, so there will be a barbell effect, and those building startups must adapt their game plan and strategy. In the SMB segment of the market, 65% of users have not chosen a core platform, which will play into the dynamic of how and when they adopt generative AI-powered point solutions. While I don’t think we will see full market consolidation for another five to 10 years, these trends will have big implications for people at every range of scale and level of maturity.
Rick Hellers: We should all be aware of the fallout from consolidation. Some of the vendors that look exciting now may not be able to survive, or they may be consolidated and have their brands removed.
Ari Kaplan: What an honor to do this with you. Thank you all so much for joining.
Listen to the complete interview at Reinventing Professionals.
Ari Kaplan regularly interviews leaders in the legal industry and in the broader professional services community to share perspective, highlight transformative change and introduce new technology at his blog and on iTunes.
This column reflects the opinions of the author and not necessarily the views of the ABA Journal—or the American Bar Association.
