Host – Reinventing Professional Services by Ari Kaplan

The Advantages of Using an AI Agent in Contract Review

November 20, 2025

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.

How Legal Professionals Can Prevent Hallucinations and Build Trust in Legal AI

November 12, 2025

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.

*Special Episode* Featuring Caroline Hill, Editor-in-Chief of Legal IT Insider, on Charting Change in Legal Ep 49

November 7, 2025

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.

Best Practices for Building a Strong Team of Lawyers and Legal Professionals to Enhance Law Firm Growth

November 5, 2025

I spoke with Howard Ankin, the Founder of Ankin Law, a personal injury and workers’ compensation law firm based in Chicago. We discussed the best practices for building a strong team of lawyers and legal professionals to enhance law firm growth, how technology can enhance client service, and how trial work will change in an AI-centric future.

Mixtape: 2025 Knowledge Management & Innovation for Legal Conference

November 3, 2025

Thanks to these industry leaders for speaking with me for my 2025 Knowledge Management & Innovation for Legal (KM&I) conference mixtape:

Michelle Gleason, Regional Sales Manager at LexisNexis, Conan Hines, Director of Practice Innovation at Fried Frank, Kevin Klein, Co-Founder at Legal Tech Connect, Katya Linossi, Co-Founder and CEO at Atlas by ClearPeople, Kyle Poe, VP of Legal Innovation and Strategy at Legora Daniel Porus, Chief Commercial Officer at Legatics, Maureen Schlade, Director of Key Accounts at LexisNexis, Ryan Steadman, Global Commercial Leader at Epiq Law Advisory, and Ben Wightwick, Chief Commercial Officer at Autologix.

Mixtape: 2025 Association of Corporate Counsel Annual Meeting

October 31, 2025

It was a privilege to interview these leaders for this mixtape from the 2025 Association of Corporate Counsel Annual Meeting: Michael Babitsky, Head of Strategy and Operations, Corporate Legal, LexisNexis, Anthony Bégon, Vice President, Legal, Trellix, Daniel Bonner, Director of Client Solutions, Level Legal, Gabe Gross, Head of eDiscovery, DiliTrust, Monica Harris, Senior Product Manager, American Arbitration Association, Kyle Konz, Shareholder, Brooks Kushman, Joshua Maley, CEO and Co-Founder, Theorem Legal, Jim McGrew, Chief Client Services Officer, Ogletree Deakins, Ashley Miller, General Counsel, Financial Services, North America, and Head of Legal Operations, Americas, Capgemini, Mark Nastasi, Founder and CEO, CobbleStone Software, Janice Ryan, Partner, Venable, and Jeni Turner, Director, Go-to-Market Strategy and Client Engagement, Corporate Legal, LexisNexis.

How KM and Legal Innovation are Shifting with the Emergence of Generative AI

October 29, 2025

I spoke with Oz Benamram, a leader in law firm knowledge management and innovation, and the Founder of SKILLS.law. We discussed the advisory services most in demand for law firms, how KM and legal innovation are shifting with the emergence of generative AI, the evolution of SKILLS.law, the likely impact of AI on legal, and the Michael Mills Memorial LegalTech Scholarship at Cornell Tech.

Midsize Law Firms are Balancing Potential and Pitfalls in Charting an Unpredictable Path Forward

October 27, 2025

I spoke with Olivia Mockel, the Chief Brand and Market Strategy Officer at SurePoint Technologies, Debbie Foster, the CEO of Affinity Consulting Group, and Laura Wenzel, the Global Marketing & Insights Director at iManage. The three companies are part of a consortium that supported a new market research report featuring the perspectives of midsize law firm leaders called “Midsize Law Firms Are Balancing Potential and Pitfalls in Charting an Unpredictable Path Forward.” We discussed how chief financial officers, chief operating officers, chief information officers, and executive directors are approaching generative AI, data and financial intelligence, technology adoption, and training to help drive their firms into a new era of legal services. Download a copy of the executive summary here: http://bit.ly/4oAO3PV.

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