Reinventing Professionals

I spoke with Matt Basile , the CEO of Naya Software , a software company that automates the legal aspects of originating commercial real estate loans for law firms and institutional lenders. We discussed building a software company while working full-time as a lawyer, new ways law firms are leveraging artificial intelligence, and whether now is the best time to begin practicing law.

I spoke with Cristin Traylor , the Senior Director of AI Transformation and Law Firm Strategy at Relativity , a legal data intelligence company that builds technology to help users organize data, discover the truth, and act on it. We discussed the release of aiR for Case Strategy, how it compares with other AI solutions in legal, and how it will affect the day-to-day work of litigation professiona...

Thanks to the following leaders for speaking with me for this mixtape at Legalweek on Day 4: Bill Roberts , Head of Corporate Communications. Disco Dennis Garcia , Vice President and General Counsel, Litera Joey Seeber , CEO, Level Legal Mary Miller , Chief Marketing Officer, KLDiscovery Rob Kwiatkowski , Founder, Discernis Tim Brady , CEO, Colligo Timo Karakashev , Founder and CEO, Cosmonauts

Thanks to the following leaders for speaking with me for this mixtape at Legalweek on Day 3:  Joshua Schnoll , Chief Marketing Officer, Everlaw Ashley Allman , Senior Director, FTI Technology Beau Wysong , SVP of Marketing, Opus 2 Bryant Bell , Lead Product Marketer - eDiscovery, Exterro Michael Connor , Chief Revenue Officer, Cimplifi Narin Olsson Akay , Director of Marketing, DeepJudge Rick Webe...

Thanks to the following leaders for speaking with me for this mixtape at Legalweek on Day 2:   Sean Fitzpatrick , CEO, Global Legal, LexisNexis Alon Dolev , Co-Founder and CEO, Maeven Chad Pinson , CEO, HaystackID Dan Malgran , Vice President of Marketing, Steno David Schnurman , CEO, Lawline John Bartman , Co-Founder, Law Tech Consultancy Keao Caindec , CEO, Clarra Oyango Snell , President and CE...

Thanks to the following leaders for speaking with me for this mixtape at Legalweek on Day 1: Kevin Clark , Right Discovery Richard Gorelick , ChronoTracer Steve Salkin , ALM Danny Thankachan , CaseGuild Jessie Torres , McDermott, Will & Schulte Remco Visser , Saga Emma Raimi-Zlatic , Smokeball

I spoke with Raj Chandrasekar , the Chief Technology and Innovation Officer of Consilio , a provider of e-discovery, document review, flexible legal talent, and legal advisory and transformation services. We discussed the biggest disruptions in the legal industry, how legal teams can leverage AI to improve and accelerate their investigations, and the most critical decisions humans still need to ma...

I spoke with Matt Mahon , the Vice President for Client Solutions at Level Legal , a concierge digital forensics, e-discovery, and managed review partner for law firms and corporate legal departments. We discussed how AI is changing e-discovery, the value of tailoring the client experience, the most interesting challenges involving emojis, and Legalweek 2026.

In this 54th episode of Charting Change in Legal, Caroline Hill , Editor and Publisher of  Legal IT Insider , and I discussed preparing for Legalweek 2026, reallocating legal work, and formalizing vibe coding.

I spoke with Sanjay Kamlani , the Founder and CEO of FairPlay . We discussed the emergence of AI-first law firms, how they differ from traditional law firms, and FairPlay's long-term vision.

I spoke with Josh Aaron , the CEO of Aiden Technologies , a company that delivers intelligent Windows endpoint automation and rapid recovery for law firms and other highly regulated organizations, which just launched AidenRescue. We discussed how AidenRescue helps law firms recover from ransomware or system attacks, the biggest endpoint management and recovery pain points in law firms, and how exp...

I spoke with Ville Kulmala , the Head of Technology Strategy and International Growth at BestSign , which delivers trusted e-signatures and legal AI for companies operating across borders. We discussed the patterns from the dot-com era and the financial crisis that are similar to the emergence of AI, how AI is changing business operations for multinational companies, and the trends legal industry...

I spoke with Matthew Bady , a registered nurse and the founder of BoardWise , a SaaS platform that helps licensed professionals manage their board paperwork. We discussed how BoardWise fits within the broader legal tech and access-to-justice landscape, and ways that the platform is evolving as more licensed professionals turn to technology to navigate changes in administrative law.

I spoke with Sam Davidoff , the Founder and CEO of Align , a digital binder product for litigators. We discussed the genesis of Align, where non-AI legal technology tools fit into a law firm’s suite of applications, and how legal tech is transforming the practice of law.

In this 53rd episode of Charting Change in Legal, Caroline Hill , Editor and Publisher of  Legal IT Insider , and I discussed Groundhog Day, law firms embracing vibe coding, and corporate counsel perspectives on AI and innovation.

I spoke with  Aku Sorainen , the Founder and Senior Partner at Sorainen , a law firm based in Estonia, with additional offices in Latvia and Lithuania. We discussed the importance of data in measuring the effects of innovation, how law firm leaders should prepare for the future of legal practice enhanced by AI, the firm’s development of Crespect , and the value of law firms spinning off their tech...

I spoke with Joey Seeber , the CEO of Level Legal , a managed services provider and subscriber to the 2025 E-Discovery Unfiltered report. We discussed how Level Legal distinguishes its approach to managed services, ways that AI is affecting the way it serves its clients, and the most compelling findings from the 2025 E-Discovery Unfiltered report.

I spoke with Matteo Pagani , the Founder and CEO of Co-Flo Enterprise , an iManage strategic technology partner. We discussed how corporate legal teams are effectively leveraging document management, the importance of operational intelligence in today’s AI-enabled legal department, and how AI is affecting the ways enterprises use and access their data.

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 fro...

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...