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 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.

I spoke with Kevin Klein, Co-Founder of LegalTech Connect and Head of Content & Programming at the KM&I for Legal Conference, and Patrick DiDomenico, who founded InspireKM Consulting and KM&I, and is now Co-Founder at LegalTech Connect. We discussed the convergence of KM&I and LegalTech Connect, the evolution of law firm knowledge management and innovation, and how conversations about KM and AI will drive the legal profession forward.

I spoke with Tom Martin, the founder and CEO of LawDroid, an Adjunct Professor teaching Generative AI and the Delivery of Legal Services at Suffolk Law School, and a co-founder of the American Legal Technology Awards. We discussed the most exciting opportunities AI is creating for lawyers, best practices for persuading AI skeptics, the ethical and practical guardrails lawyers should consider, and the objective of the American Legal Technology Awards.

It was a privilege to speak with these leaders for this Relativity Fest 2025 mixtape:   Brett Chalmers, Website and Product Marketing Director, Opus 2. Mathew Corfield, Surveillance Product Owner, Theta Lake. Blake Ferger, Senior Consultant, Complete Discovery Source. Shawn Gaines, Chief Marketing Officer, OnDean. Frank Perrone, Founder and CEO, ReVia Matt Rosenthal, Senior Vice President of Sales, Cimplifi. Alex Sappington, Co-CEO, Page Vault. Ben Sexton, Senior Vice President, Innovation and Strategy, JND Legal Administration. Marcin Święty, Chief Security Officer, Relativity. Alston Walker, Senior Discovery Consultant and Executive Client Services Liaison, HaystackID. Freya Zhou, Co-Founder & COO, Fileread.

I spoke with Binit Agrawal, the Chief of Staff at Lucio, an India-based AI-native workspace for lawyers. We discussed the pitfalls of using AI in a legal practice, the mindset and skill set that junior lawyers should adopt, and how AI in the legal profession is evolving.

I spoke with Timothy Keith, the Founder and CEO of Propense.ai, which develops technology to empower cross-selling in professional services, including at law firms. We discussed how AI can help law firms improve cross-selling, the most common business development challenges they face, and where lawyers should leverage technology to enhance their business development.

I spoke with Matt Patel, Founder and Chief Operating Officer at Malbek, an enterprise CLM company providing comprehensive contract management solutions for procurement, legal, sales, and other functions. We discussed who gains the most value from CLM, how its value has changed since the emergence of generative AI, and how it is evolving.

I spoke with Cecy Graf and T.J. Henry, the co-founders of Federate, which builds and manages back-office systems like billing, finance, and operations for small and mid-size law firms. We discussed strategic opportunities in back-office support for law firms, how law firms can drive operational efficiency, techniques for facilitating innovation while managing risk, and emerging trends that managing partners should prepare for.

I spoke with Rebecca Stidham, a tax partner and the Law Firm Services Team Leader at Withum, Smith+Brown, PC, an accounting and advisory firm that provides tax, assurance, accounting, digital transformation, cybersecurity, and wealth management services to law firms, among other sectors. We discussed how law firm leaders can drive growth and profitability, key areas for enhancing digital transformation, and best practices for keeping up with the rapid pace of legal technology development.

I spoke with Nishat Mehta, the CEO of Lexitas, a provider of court reporting, records retrieval, process service, and legal talent solutions. We discussed how AI is impacting traditional legal services, what lawyers can do to prepare for the transition to a more AI-centric profession, the pitfalls attorneys must avoid, and future opportunities for the application of AI in legal.

I spoke with Brandon Hollinder, the Vice President of eDiscovery and Cyber Solutions at Epiq, a provider of legal and business services. We discussed the proactive steps companies should take to strengthen their information governance, how AI-driven data mapping and labeling tools are changing the way companies understand and manage their data risk, and ways that AI is affecting cybersecurity.