I spoke with Eric Greenberg, the Executive Vice President and General Counsel of Cox Media Group, a multi-platform media company based in Atlanta. Eric was a finalist for Corporate Counsel magazine's General Counsel of the Year in 2024 and 2025 and is the author of an eight-part series on AI in Bloomberg Law. We discussed how general counsel can begin leveraging AI, how to help lawyers shift from linear to non-linear thinking, and how law firms can support their clients' digital transformation journey.

I was honored to feature these dynamic legal industry leaders for the Q4 2025 Ari Kaplan Advisors CEO Roundtable, focusing on the transformation of the profession in 2026: Chris Combs, LinkSquaresNnamdi Emelifeonwu, DefinelyDebbie Foster, Affinity Consulting Group Paulina Grnarova, DeepJudge Jennifer Hill, ThoughtRiver Mark Nastasi, CobbleStone SoftwareMatteo Pagani, Co-Flo Enterprise

I was honored to interview these remarkable leaders for the inaugural Ari Kaplan Advisors Legal Tech GC/CLO Roundtable, focusing on the key challenges, trends, and opportunities that are likely to affect strategic priorities in 2026: Jason Barnwell, AgiloftMarla Crawford, CimplifiClint Crosier, iManageDennis Garcia, LiteraJenny Hamilton, ExterroBeth Kallet-Neuman, RelativityColin Levy, MalbekJohn Patzakis, X1JP Son, Verbit

I spoke with Raymond Mieszaniec, Co-Founder and Chief Operating Officer of EvenUp, a legal tech company that uses AI to help personal injury attorneys maximize case values. We discussed why plaintiffs' personal injury work is well-suited to AI-driven automation, how AI tools will affect the volume and quality of cases filed, and how AI is changing the practice of law.

In this 51st episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I looked back at developments in 2025 and ahead to 2026.

I spoke with Jenn McCarron, the Co-Founder & CEO of Contracts.ai, a platform that bridges the data gap between legal and finance by transforming contracts into structured, actionable intelligence powering enterprise decision-making. We discussed the technology development process, how Contracts.ai differs from a CLM and a legal AI tool, and advice for legal teams pursuing digital transformation.

I spoke with Ravi Tandon, the CEO and Co-Founder of DecoverAI, a legal intelligence platform that helps attorneys uncover insights during investigations and e-discovery. We discussed the biggest gaps in law firm knowledge management today, how AI is transforming investigations and e-discovery, ways that legal professionals can build trust, reliability, and responsible AI practices for high-stakes legal matters, and where the use of Agentic tools in legal is headed.

I spoke with James Barclay, the CEO of Passle, a legal-tech company that supports lawyer-authored thought leadership and helps firms use content for revenue growth. We discussed why cross-selling is important for law firms, how CrossPitch AI differs from traditional KM/experience-management tools, the benefits of integrating laterals and other attorneys into the cross-selling process, and where thought leadership creates the most leverage for cross-selling.

I spoke with Dennis Meador, the Founder and CEO of the Legal Podcast Network. We discussed why podcasting has become a powerful marketing tool for legal professionals, the hallmarks of a successful podcast, and how to overcome the challenges of launching and maintaining a podcast in the legal sector.

In this 50th episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I discussed the prospect of an AI bubble, innovation and client service, and proactively driving change.

I spoke with Matt Lhoumeau, the Co-Founder and CEO of Concord, a contract lifecycle management software platform. We discussed how AI  is changing the way legal teams leverage CLM, the launch of Horizon, Concord's conversational AI platform, why managing contracts manually is still common, and how CLM will evolve.

I spoke with Alex Zilberman, the Co-Founder and CEO of Chamelio, a legal intelligence platform for corporate legal departments. We discussed how AI is changing the way corporate legal teams practice, where they are finding success with AI, where they are still facing challenges, and best practices for driving adoption of new applications.

I spoke with Ned Gannon, the co-founder and CEO of Coheso, an AI-native legal front door and work management platform for in-house legal and compliance teams. We discussed the biggest barriers to AI adoption for corporate legal professionals, lessons that legal tech founders should keep in mind as they grow their businesses, and the non-negotiable elements of responsible AI in the legal domain.

I spoke with Melanie Herschorn, the founder of Big Impact Books, a publisher and book marketing strategist who helps attorneys and professionals become authors and recognized experts in their field. We discussed the greatest opportunities for lawyers to leverage a book to grow their practice, how lawyers can balance their client work with the demands of writing and promoting a book, and the effect of AI on publishing.

I spoke with Brian Powers, the Co-Founder & CEO of Markups.ai, a company that created an AI agent called Agent Marko to draft, revise, and analyze contracts from clients’ inboxes, with no new platform required, and Debbie Epstein Henry, the Founder of DEH Consulting, Speaking, and Writing, and the Chief Strategic Advisor to Markups.ai. We discussed the advantages of using an AI agent in contract review, where startups can distinguish themselves in a crowded market, the misconceptions about AI that leaders need to address before they can achieve broad adoption, and the skills legal professionals should enhance to fuel their success.

I spoke with Doug Bemis and Chris Martin, the CEO and President, respectively, of Syntracts, a legal AI company that offers a secure, on-premises contract intelligence platform. We discussed the unique security and privacy challenges for AI in large law firms, how legal teams are adapting, and where legal AI is headed.

I spoke with Brandie Knox, the Principal & Creative Director of Knox Design Strategy, a consultancy that partners with law firms on branding, user experience, and user interface design. She is also the Founder & CEO of Moxx, a digital case notebook that helps litigators streamline case preparation and collaboration. We discussed best practices in legal to leverage design to stand out, and how the intersection of design, strategy, and technology is shaping the future of legal practice.

I spoke with Mark Doble, the Founder and CEO of Alexi, an AI-driven legal workflow platform. We discussed how legal professionals can prevent hallucinations and build trust in legal AI, the top privacy and compliance risks that law firms need to consider, and how generative AI will transform legal workflows.

Thanks to these industry leaders for speaking with me for my 2025 LegalTech Connect conference mixtape: James Lee, CEO, LegalMation; John DiMenna, Sales Director, Dealcloser; Moiz Shirazi, Co-Founder and CEO, SCOREalytics, Inc; Nicole Bradick, Global Head of Innovation, Factor; and, Scott Mozarsky, CEO and Managing Director, JEGI LEONIS.

In this 49th episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I discussed Legal IT Insider’s 30th anniversary, the first Orange Rag, the potential for an AI bubble, and emerging AI leadership.