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The business of providing professional advice is changing. Today, anyone can go online and access a wealth of information about any topic, from legal and medical advice to financial planning and accounting suggestions. This blog is designed to offer ideas, guidance, and perspectives on how to effectively navigate a perpetually shifting professional landscape, with a unique focus on the legal industry and the technology that is driving its evolution.
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I spoke with Olivia Mockel, the Chief Brand and Market Strategy Officer at SurePoint Technologies, Debbie Foster, the CEO of Affinity Consulting Group, and Laura Wenzel, the Global Marketing & Insights Director at iManage. The three companies are part of a consortium that supported a new market research report featuring the perspectives of midsize law firm leaders called "Midsize Law Firms Are Balancing Potential and Pitfalls in Charting an Unpredictable Path Forward." We discussed how chief financial officers, chief operating officers, chief information officers, and executive directors are approaching generative AI, data and financial intelligence, technology adoption, and training to help drive their firms into a new era of legal services.
In this 48th episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I discussed the value of practical conversations about AI pricing, promoting wellness at conferences, and empowering change.
I spoke with Capri Miller and Matt Mahon, the Customer Partner and Vice President of Customer Experience, respectively, at Level Legal, a provider of managed services, about the Association of Corporate Counsel's 2025 Annual Meeting in Philadelphia and how corporate legal departments are evolving.
I spoke with Kevin Klein, Co-Founder of LegalTech Connect and Head of Content & Programming at the KM&I for Legal Conference, and Patrick DiDomenico, who founded InspireKM Consulting and KM&I, and is now Co-Founder at LegalTech Connect. We discussed the convergence of KM&I and LegalTech Connect, the evolution of law firm knowledge management and innovation, and how conversations about KM and AI will drive the legal profession forward.
I spoke with Tom Martin, the founder and CEO of LawDroid, an Adjunct Professor teaching Generative AI and the Delivery of Legal Services at Suffolk Law School, and a co-founder of the American Legal Technology Awards. We discussed the most exciting opportunities AI is creating for lawyers, best practices for persuading AI skeptics, the ethical and practical guardrails lawyers should consider, and the objective of the American Legal Technology Awards.
It was a privilege to speak with these leaders for this Relativity Fest 2025 mixtape:
Brett Chalmers, Website and Product Marketing Director, Opus 2.
Mathew Corfield, Surveillance Product Owner, Theta Lake.
Blake Ferger, Senior Consultant, Complete Discovery Source.
Shawn Gaines, Chief Marketing Officer, OnDean.
Frank Perrone, Founder and CEO, ReVia
Matt Rosenthal, Senior Vice President of Sales, Cimplifi.
Alex Sappington, Co-CEO, Page Vault.
Ben Sexton, Senior Vice President, Innovation and Strategy, JND Legal Administration.
Marcin Święty, Chief Security Officer, Relativity.
Alston Walker, Senior Discovery Consultant and Executive Client Services Liaison, HaystackID.
Freya Zhou, Co-Founder & COO, Fileread.
I spoke with Matt Patel, Founder and Chief Operating Officer at Malbek, an enterprise CLM company providing comprehensive contract management solutions for procurement, legal, sales, and other functions. We discussed who gains the most value from CLM, how its value has changed since the emergence of generative AI, and how it is evolving.
I spoke with Brandon Hollinder, the Vice President of eDiscovery and Cyber Solutions at Epiq, a provider of legal and business services. We discussed the proactive steps companies should take to strengthen their information governance, how AI-driven data mapping and labeling tools are changing the way companies understand and manage their data risk, and ways that AI is affecting cybersecurity.
In this 47th episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I discussed Legal IT Insider's 30th anniversary, reimagining billable work, anticipating disruption, and providing value.
I spoke with John Lee, the General Counsel and Head of Strategy for Ruli, a legal AI platform for corporate law departments. We discussed how legal teams should calculate the ROI or value of a legal technology investment, the qualities buyers should consider when selecting a legal AI vendor, and ways that client expectations have changed due to advanced AI transparency, speed, and cost-efficiency.
I spoke with Karl Schieneman, a Co-Founder of TestMyWitness, which empowers witness preparation using AI. We discussed how legal teams can leverage technology to prepare witnesses to testify, and how that process is evolving.
I spoke with Anne Post, CEO of Xakia, North America, a provider of legal matter and contract management solutions. We discussed how law department leaders should approach technology adoption to maximize impact and efficiency, the biggest challenges in-house legal teams face in demonstrating value, and the most compelling opportunities for legal departments to become true strategic partners within their organizations.
In this 46th episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I discussed budgeting, purchasing, and piloting in legal tech, measuring ROI and value, and building community.
I spoke with Diane Homolak, the VP of Technology Solutions for Integreon, Sylvain Magdinier, an independent consultant specializing in legal transformation and innovation, and Gayle Gorvett, the CEO and Managing Director of GGorvett Consulting. They are all part of a workstream within RAILS that helped further the deployment and development of AI in the legal profession. We discussed how in-house counsel can use the RAILS Risk Framework to better approach AI risk assessment and governance, and ways that legal teams are managing AI risk, along with privacy and cybersecurity.
I spoke with Oyango Snell, the Executive Director of the Corporate Legal Operations Consortium. We discussed the biggest challenges facing leaders in legal operations, how they can more effectively highlight their contributions to their organizations, the value of operational maturity skills, and the skills necessary for legal operations leaders to thrive.
I spoke with Kevin Broyles, the co-founder and managing partner of FisherBroyles, a distributed law firm. We discussed how legal teams can empower collaboration, maintain culture, and ensure accountability with remote teams, the professional, personal, and financial benefits of a distributed law firm model, and best practices for driving law firm growth in a rapidly changing environment.
I spoke with Sagi Eliyahu, the CEO and co-founder of Tonkean, a process orchestration platform, and the maker of LegalWorks, which helps legal teams automate complex processes and time-consuming workflows. We discussed the best practices for legal teams looking to adopt AI, the difference between how legal teams are using generative AI and agentic AI, and misconceptions about the capabilities of AI.
I spoke with Monica Winghart and Doug Luftman, the Founders of Velocity Edge Advisors, a San Francisco-based legal and HR services firm. We discussed the value of combining on-demand legal and HR services, the rising interest in fractional GC services, and the importance of understanding a client's business to exceed expectations.
I spoke with Nick Abrahams, a partner and the Global Co-Leader of Digital Transformation at Norton Rose Fulbright, who is also the Co-Founder of LawPath, a direct-to-consumer legal services provider. We discussed balancing digital transformation and practicing law, the effect of generative AI on the legal profession, and the qualities that matter most to prospective clients.
In this 45th episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I discussed ILTACON 2025, the Copilot gateway to generative AI, and transforming legal training.
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