Reinventing Professionals

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 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 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 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 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.