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 when 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 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.