Reinventing Professionals

Brian Powers, Co-founder and CEO of Markups.ai, develops AI agents for contract review. Debbie Epstein Henry, Founder of DEH Consulting, brings her legal innovation expertise to the discussion. They explore how AI can streamline contract processes, debunk common misconceptions about AI capabilities, and advise on startup differentiation through personalized services. Both emphasize the importance of legal professionals enhancing their skills, particularly in communication and strategic thinking, to thrive alongside AI advancements.

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.

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.

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.

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

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.

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.

I spoke with Rick Hellers, the CEO of Scan Logic, the provider of BillSync and APSync, designed to simplify law firm finances. We discussed the most common financial challenges law firms face, how leaders are using technology to address them, best practices for ensuring prompt and full payment of legal invoices, and how the economy is affecting the financial health of law firms.

In this 48th episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I discussed the value of practical conversations about AI pricing, promoting wellness at conferences, and empowering change.

I spoke with Capri Miller and Matt Mahon, the Customer Partner and Vice President of Customer Experience, respectively, at Level Legal, a provider of managed services, about the Association of Corporate Counsel's 2025 Annual Meeting in Philadelphia and how corporate legal departments are evolving.