Reinventing Professionals

I spoke with Vicente Silveira, the Co-Founder and CEO at AI Drive, a platform for legal professionals and teams to deploy agents that support document-intensive projects. We discussed the importance of trust and accuracy in AI-powered legal document analysis, the value of a multi-model approach, and where AI agents in legal work are headed.

In this 56th episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I discussed the 10th Anniversary of the Lexpo Conference, best practices for assessing the value of legal AI investments, and the LexisNexis AI Symposium on May 5th in New York City.

I spoke with Bill Schroeder, the founder and co-principal of Clarity, a consultancy focused on brand research, brand strategy, and brand-driven change programs for law firms. We discussed how law firm branding is unique, the effect of brand-driven change programs, and branding advice for law firm managing partners.

I spoke with Nick Fleisher, the Co-Founder and CEO of Sandstone, an AI-native control tower for corporate legal departments. We discussed how Sandstone differs from Contract Lifecycle Management tools, the biggest challenges of introducing new technology in a corporate legal department, and how technology is transforming the way in-house legal teams operate.

I spoke with Nick West, a Partner and the Chief Strategy Officer at Mishcon de Reya. We discussed the firm's approach to innovation, the metrics it captures related to its use of Legora, how it measures the ROI of Legora and other tools, how law firms should think about the return on their technology investments, and the new Legora ROI Report.

In this 55th episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I discussed our impressions of Legalweek 2026, the ROI of legal AI, and the maturation of AI deployment in law firms and corporate legal departments.

I spoke with Pat Utz, the Co-Founder and CEO of Abstract, an AI policy intelligence platform for legislation and regulation. We discussed how Abstract sources its information, how customers use it to understand state and federal regulations, the unique type of intelligence it provides, and the importance of guardrails for relying on the output of AI-assisted technology.

I spoke with Alex Sappington, the Co-CEO of PageVault, a tool for capturing online content in a legally defensible manner. We discussed PageVault’s launch of Stencil, the problem Stencil solves for trademark teams, how PageVault’s work in litigation strengthens its role in trademarks, and where Stencil fits within the broader array of legal technology tools.

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 professionals.

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 Weber, Managing Partner, Arbor Ridge Partners Rion Walker, VP of Corporate Development, BARBRI Tom Baldwin, Founder and CEO, Entegrata

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 CEO, Corporate Legal Operations Consortium Peter Zver, Vice President of Revenue and Operations, Bundledocs Shai Mehani, Co-Founder and CEO, In-House Connect

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 make in an AI-driven workflow.

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 expectations for cybersecurity and endpoint recovery are evolving.

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 leaders should track.

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 technology.

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 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

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, Malbek John Patzakis, X1 JP Son, Verbit

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.

I spoke with Ravi Tandon, the CEO and Co-Founder of DecoverAI, a legal intelligence platform that helps attorneys uncover insights during investigations and e-discovery. We discussed the biggest gaps in law firm knowledge management today, how AI is transforming investigations and e-discovery, ways that legal professionals can build trust, reliability, and responsible AI practices for high-stakes legal matters, and where the use of Agentic tools in legal is headed.

I spoke with James Barclay, the CEO of Passle, a legal-tech company that supports lawyer-authored thought leadership and helps firms use content for revenue growth. We discussed why cross-selling is important for law firms, how CrossPitch AI differs from traditional KM/experience-management tools, the benefits of integrating laterals and other attorneys into the cross-selling process, and where thought leadership creates the most leverage for cross-selling.

I spoke with Dennis Meador, the Founder and CEO of the Legal Podcast Network. We discussed why podcasting has become a powerful marketing tool for legal professionals, the hallmarks of a successful podcast, and how to overcome the challenges of launching and maintaining a podcast in the legal sector.

In this 50th episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I discussed the prospect of an AI bubble, innovation and client service, and proactively driving change.

I spoke with Matt Lhoumeau, the Co-Founder and CEO of Concord, a contract lifecycle management software platform. We discussed how AI  is changing the way legal teams leverage CLM, the launch of Horizon, Concord's conversational AI platform, why managing contracts manually is still common, and how CLM will evolve.

I spoke with Alex Zilberman, the Co-Founder and CEO of Chamelio, a legal intelligence platform for corporate legal departments. We discussed how AI is changing the way corporate legal teams practice, where they are finding success with AI, where they are still facing challenges, and best practices for driving adoption of new applications.

I spoke with Ned Gannon, the co-founder and CEO of Coheso, an AI-native legal front door and work management platform for in-house legal and compliance teams. We discussed the biggest barriers to AI adoption for corporate legal professionals, lessons that legal tech founders should keep in mind as they grow their businesses, and the non-negotiable elements of responsible AI in the legal domain.

I spoke with Melanie Herschorn, the founder of Big Impact Books, a publisher and book marketing strategist who helps attorneys and professionals become authors and recognized experts in their field. We discussed the greatest opportunities for lawyers to leverage a book to grow their practice, how lawyers can balance their client work with the demands of writing and promoting a book, and the effect of AI on publishing.

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 Doug Bemis and Chris Martin, the CEO and President, respectively, of Syntracts, a legal AI company that offers a secure, on-premises contract intelligence platform. We discussed the unique security and privacy challenges for AI in large law firms, how legal teams are adapting, and where legal AI is headed.

I spoke with Brandie Knox, the Principal & Creative Director of Knox Design Strategy, a consultancy that partners with law firms on branding, user experience, and user interface design. She is also the Founder & CEO of Moxx, a digital case notebook that helps litigators streamline case preparation and collaboration. We discussed best practices in legal to leverage design to stand out, and how the intersection of design, strategy, and technology is shaping the future of legal practice.

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.

Thanks to these industry leaders for speaking with me for my 2025 LegalTech Connect conference mixtape: James Lee, CEO, LegalMation; John DiMenna, Sales Director, Dealcloser; Moiz Shirazi, Co-Founder and CEO, SCOREalytics, Inc; Nicole Bradick, Global Head of Innovation, Factor; and, Scott Mozarsky, CEO and Managing Director, JEGI LEONIS.

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.