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
Ari Kaplan Advisors
Ari Kaplan, a leading legal industry analyst, is an inaugural Fastcase 50 honoree, a finalist for ILTA’s Thought Leader of the Year award, and a fellow of the College of Law Practice Management. His most recent book, Reinventing Professional Services: Building Your Business in the Digital Marketplace, was released in Japanese, and West Academic published the second edition of The Opportunity Maker: Strategies for Inspiring Your Legal Career Through Creative Networking and Business Development in 2016.
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Branding Advice for Law Firm Managing Partners
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…
How Technology is Transforming the Way In-House Legal Teams Operate
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…
Measuring the ROI of Legal AI in Practice
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*Special Episode* Featuring Caroline Hill, Editor-in-Chief of Legal IT Insider, on Charting Change in Legal Ep 55
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…
The Importance of Guardrails to Rely on the Output of AI-Assisted Technology
Leveraging Technology to Draft Trademark Applications and Process Renewals
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…
Building a Software Company While Practicing Law Full-Time
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…
Transforming the Application of AI in E-Discovery
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…
Legalweek 2026 Day 1 Mixtape
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 &