Year in Review

CEO Roundtable With Ari Kaplan: Legal industry CEOs share perspectives on 2023, vision for 2024

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Ari Kaplan talks with his 2023 CEO roundtable.

Industry analyst Ari Kaplan recently hosted the 2023 Ari Kaplan Advisors CEO roundtable and spoke with leading CEOs about opportunities, challenges and the road ahead in the legal industry.

Sheryl Hoskins: I am the CEO of Litera, a leading provider of software tools that help lawyers, partners and other legal professionals focus on their craft.

Aviva Cuyler: I am the CEO of JD Supra, which provides content marketing and business intelligence derived from the consumption of that content to the legal and related industries.

Debbie Foster: I am the CEO of Affinity Consulting, which works with law firms of all sizes on business transformation and digital transformation, helping them get their work done more efficiently.

Josh Blandi: I am the CEO of UniCourt, which provides legal data services for real-time access to court dockets and analytics through our APIs.

Anna McGrane: I am the CEO of PacerPro, which focuses on enterprise data for large law firms in the court filing space.

Eric Thurston: I am the CEO of SurePoint Technologies, which offers practice management and accounting solutions for midsize law firms.

Rudy DeFelice: I am the CEO of KP Labs, which helps corporate legal departments on their digital transformation journey through workflow automation and AI-based contract intelligence.

Nicole Clark: I am the CEO of Trellis, a state trial court data and analytics company.

Early Stephens: I am the CEO of Actionstep, a cloud-native practice management and financial platform for midsize law firms.

Kelly Griswold: I am the CEO of Onna, which works with enterprise corporate legal and IT departments to manage unstructured data from content, communication and collaboration apps that is ultimately used for discovery, investigations, litigation and now AI-powered workflows.

Daniel Lewis: I am the CEO of LegalOn in the United States. We also operate in Japan and are a company that provides AI contract review to help in-house legal teams with presignature contract reviews.

Josh Baxter: I am the CEO of NetDocuments, a leading content management platform for the legal industry in the cloud, supporting a wide range of legal professionals’ work activities across the document lifecycle.

Matt Sunderman: I am the CEO of Harbor.

Julie Lewis: I am the CEO of Digital Mountain, which is a global digital forensics, e-discovery and cybersecurity company.

Ari KaplanAri Kaplan. Photo by Tori Soper.

Ari Kaplan: Where have you seen a new opportunity this year?

Debbie Foster: Our focus is really on helping law firms get the most out of the technology they already own and are purchasing by supporting them beyond deployment and training.

Rudy DeFelice: Every day, we see a gen AI article AI washing every company that has leased a computer, but it has oxygenated the whole space around technology and innovation, so we are finding that clients that had projects on the back shelf now have the institutional latitude to do those things. Their executive committees are interested in supporting gen AI and innovation, so we are revisiting those projects. If there is something that was stalled, this might be a good opportunity to revive it.

Anna McGrane: Technology is not always the solution. While there is a question about whether the industry is ready for generative AI, it is creating a space for conversations and openness, so there is an opportunity for us to jump-start projects that enable the necessary change to happen. We have spent 10 years building a data machine, and there are now more companies that are interested in enterprise-level data as they’re trying to use gen AI on more projects.

Daniel Lewis: In our surveys and other survey data, there is an incredible amount of optimism and excitement from lawyers themselves, which feels very different from behaviors of the last 10 years. The level of excitement of lawyers over learning more about AI and benefiting from it is markedly different than I have ever seen. I am incredibly excited about the opportunities associated with generative AI, and the change in legal technology that we will see over the next 10 years will be so much more expansive than what we saw in the last 10. In contract review, it feels like manna from heaven and is a step change in capabilities.

Sheryl Hoskins: Not only is there a ton of excitement, but there are a lot of ideas emerging in firms about how to leverage generative AI, whether to accelerate a new feature within an existing product or even generate new products, which is coming from customer feedback and their pain points. There is a ton of creativity around it, which is what led us to what we’re calling Project Dragon, which is a deal-point extraction solution that we will be launching shortly.

Josh Baxter: The industry has a hammer, AI, which it hopes will solve every problem, but the problems we have been solving remain in this industry. We need to stay focused on delivering on that value proposition for our customers while bringing some of these AI solutions together with our existing solutions by flowing them into the applications our users are accustomed to using and inserting them right into their workflow to make it incredibly easy to adopt. In addition, for the first time, lawyers are coming to IT and the business and asking to use AI, so the black box methodology of a vendor providing a fixed application will be problematic because firms want the flexibility to customize and modify those applications.

Early Stephens: Firms are realizing that they have decades of technical and operational atrophy, which they now need to address to survive, which represents a big opportunity, especially as more senior lawyers retire. They are relying more on generative AI to engage in intuitive automation that codifies the intellectual brilliance of their firm and incorporates solutions that can run automatically. We have an insurance defense customer who has transformed his relationship with his insurance carriers by operating in a new level of transparency. They are improving outcomes using data analytics to make decisions.

Julie Lewis: I think generative AI is better positioned as a productivity tool, rather than a replacement for human talent. The legal industry has always worked on a billable hour model, so when tools save time and reduce the number of hours a professional needs to spend on a task, it is likely to create new pricing models, similar to how doctors work when using an MRI machine. This represents an evolutionary time for our industry. Some attorneys or legal professionals may even become prompt engineers.

Kelly Griswold: I would venture to guess that the legal technology industry over the last decade has probably processed and structured more unstructured data than any other industry, which gives it a massive advantage. When ChatGPT emerged, we recognized that it reflected a major tipping point, particularly for the legal technology industry, and built an experience for ourselves first using our technology and gen AI. We centralized all our public proprietary content, such as all-hands recordings on Zoom, help center channels and Confluence pages that talk about discounting policies, among other items that constitute the things that everybody can see but nobody can find. We put it into an Onna workspace, and the technology live-connects it, so that it is always up to date.

Josh Blandi: We have seen this massive shift in law firms looking at their data as a core asset. Generative AI now makes certain use cases for that data possible, which were not easy to implement even two or three years ago. Firms are also able to merge internal and external data for their benefit. Five years ago, firms did not look at their technology staff, and their enterprise data strategy was not the key focus that it is today.

Ari Kaplan: What concerns are you focused on addressing in 2024?

Sheryl Hoskins: One of the concerns that we are trying to help solve is education related to AI. There is buzz versus reality related to what AI tools can realistically do. We think it is super exciting, and there is great technology available, but there is also a lot of information. In fact, some general counsel are limiting the use of AI by their outside counsel based on a lack of understanding of how it works and is applied.

Josh Baxter: The industry is facing this competition between FUD and FOMO. People are really worried about pricing and how they will continue to be paid for the value that they generate when it takes a tenth of the time. Still, they recognize that to be competitive over the next three to five years, generative AI will be a meaningful part of the future of legal services. There will come a time when clients will expect their lawyers to be using generative AI to deliver work to them, so education will be even more important. 2023 was the year of hype for generative AI in the legal industry, and there is a real risk that 2024 could turn into the year of disillusionment with generative AI if we don’t help our customers through that journey by understanding how they can start to use these technologies and answering the questions that they are asking so they can prepare for 2025 and beyond.

Kelly Griswold: If we don’t focus on the outcomes it generates, then we will fall into that trap of disillusionment. If we keep talking about generative AI and we have a capabilities-led conversation, then I think that leads to a lot of discussion without much meaning or value. If, however, we can tie these capabilities to use cases and outcomes that deliver tangible results and value, then we’re going to break through and do some pretty amazing things.

Josh Blandi: The last thing we want is solutions chasing problems with generative AI because we’re so enthralled about the capabilities of what it can do, but it comes back to solving problems and using that technology to do it.

Aviva Cuyler: There’s the firm overtly using AI, and then us using AI in products that make their life better by improving those tools. From our perspective, being able to use AI to perform data analysis for our clients who want to derive conclusions from information is powerful.

Nicole Clark: Part of our job this year will be helping professionals move from experimenting with generative AI to applying it to their work. We need to help them with prompts and provide context to their data to produce useful output.

Julie Lewis: There is a dark side. A lot of collaboration software tools are using generative AI, and from a marketing standpoint, you will see an explosion of spam like we have never seen in our lifetimes. For e-discovery, that means more junk email versus real email or messages. There will also be more phishing communication that is harder to distinguish from authentic conversations. Ultimately, we will need better mechanisms to screen our emails for the data explosion that we will experience.

Ari Kaplan: What skills are necessary to thrive in 2024?

Anna McGrane: There is so much opportunity with AI, but there is also a great opportunity for disillusionment, so the ability to communicate will be more important than ever because you can more effectively align expectations on projects.

Debbie Foster: One of the biggest challenges our clients will have, which we will need to help them solve, is all around, the bar associations [are] getting involved in how they bill for the work that they do when [they] have used generative AI. So the smaller the firm, the harder this is because they don’t have the same resources as their larger peers to implement guardrails for how their lawyers should be using AI. While a larger firm has to do this across a larger scale, it does not require significantly less work to build out the process in a smaller firm. The way the bar associations are getting involved in regulating how lawyers use and bill for AI will create an incredible amount of confusion, fear and hesitancy in using tools that can make their jobs easier.

Daniel Lewis: In-house lawyers and those in small practices, maybe even those in large firms, need to think more about how technology lays a foundation for the work that they do on top of it. I do see that changing with in-house teams, where someone new to a GC role building at a growing company is thinking about how to incorporate technology that supports the team to scale more efficiently.

Kelly Lake: AI in itself is creating a huge amount of ambiguity in caselaw and a mishmash of regulation requiring trusted content that eliminates the need to second guess or double-check the work. Our clients want another level of depth, so we are using large language models to enrich the content that we have on the back end to speed up our operations and that allows us to be more responsive.

Ari Kaplan: Where do you see the industry headed?

Eric Thurston: We see less economic uncertainty and expect 2024 to be a good year with continued positive growth. For our business, we emphasize how to manage talent better and continue to create culture because we are growing organically and through M&A. We want to find key skill sets because as we try and build AI into our solutions, we want to bring proven solutions to market that are insightful. We serve many midsize law firms that may not have the resources that others do and want to have the right technologists on our side to continue to build those capabilities into our solutions that have a consistent level of innovation going into moving forward. We have analyzed how much of our solutions our customers aren’t using and want to help them with that and we are starting to pilot some AI capabilities within them. So we are optimistic for 2024 and looking forward to wrapping up this year and getting started on it.

Aviva Cuyler: As firms are using AI more, it becomes easier for them to create content, which results in more content for us to publish. We have integrated AI into our platform to make recommendations to firms based on the content that they have produced, such as the type of follow-up material that would appeal to their target readers, and also educate them on the framing, so that the content is better. The more data we have around the content, the better the guidance we can provide to our clients.

Josh Baxter: 2024 presents an opportunity for us to help our customers continue to modernize their technology stack. As generative AI solutions mature and reach real market viability, we want them to have a foundation on which they can build. Then, as we start to deliver truly exceptional generative AI solutions, they can embrace those technologies and improve on the work that they provide to their clients. Ultimately, I think both quality and productivity will improve for the entire industry as a result.

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.

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