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, LinkSquares Nnamdi Emelifeonwu, Definely Debbie Foster, Affinity Consulting Group Paulina Grnarova, DeepJudge Jennifer Hill, ThoughtRiver Mark Nastasi, CobbleStone Software Matteo 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, Agiloft Marla Crawford, Cimplifi Clint Crosier, iManage Dennis Garcia, Litera Jenny Hamilton, Exterro Beth Kallet-Neuman, Relativity Colin Levy, Malbek John Patzakis, X1 JP 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.