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.

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.