Reinventing Professionals

I spoke with David Solomon and Joe Tiano , the CEO and Co-Founder, respectively, at Legal Decoder , a legal spend analytics platform. We discussed how Legal Decoder’s analytics approach differs from traditional e-billing review or timekeeper compliance tools, the company’s investment from Trajectory Capital, and how AI is changing the way legal work is structured, priced, and delivered.

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 professiona...

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 Webe...

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 CE...

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 ma...

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 exp...

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...

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 tech...