Reinventing Professionals

In this 52nd episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I discussed expectations for 2026, the evolution of AI usage in legal, vibe coding, and perspectives on the year ahead.

I spoke with Kyle Poe, the Vice President of Legal Innovation and Strategy at Legora, a legal AI platform for law firms and legal departments. We discussed the current state of AI adoption in the legal industry, how law firms are quantifying and qualifying ROI, and how AI is influencing how firms price, package, and deliver their work.

I spoke with Daryl Fitzpatrick, the Chief Revenue Officer at Intellek, which provides learning technology to law firms. We discussed how law firms can use their learning management system beyond traditional training, ways to create additional revenue streams from training programs, and how an LMS can improve communication with clients.

I spoke with Chris DeConti, the Chief Strategy Officer at Factor, an alternative legal services provider. We discussed how AI fluency differs from knowing how to use specific tools, training lawyers who are curious but cautious about AI, and how legal professionals should shift their thinking from certainties to possibilities when working with AI.

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

In this insightful discussion, Beth Kallet-Neuman, General Counsel at Relativity, emphasizes the importance of product storytelling to highlight customer value. Marla Crawford from Cimplifi shares her experience with rapid onboarding in legal tech. Dennis Garcia, VP at Litera, talks about his role as a power user of internal products. John Patzakis, Chief Legal Officer at X1, highlights the unique challenges faced by legal tech companies regarding discovery standards, especially with the rise of AI and its impact on legal processes.

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.