I was honored to interview these remarkable leaders for the inaugural Ari Kaplan Advisors Legal Tech GC/CLO Roundtable, focusing on the key challenges, trends, and opportunities that are likely to affect strategic priorities in 2026:

Jason Barnwell, Agiloft

I spoke with Raymond Mieszaniec, Co-Founder and Chief Operating Officer of EvenUp, a legal tech company that uses AI to help personal injury attorneys maximize case values. We discussed why plaintiffs' personal injury work is well-suited to AI-driven automation, how AI tools will affect the volume and quality of cases filed, and how AI is changing the practice of law.

In this 51st episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I looked back at developments in 2025 and ahead to 2026.

I spoke with Jenn McCarron, the Co-Founder & CEO of Contracts.ai, a platform that bridges the data gap between legal and finance by transforming contracts into structured, actionable intelligence powering enterprise decision-making. We discussed the technology development process, how Contracts.ai differs from a CLM and a legal AI tool, and advice for legal teams pursuing digital transformation.

I spoke with Ravi Tandon, the CEO and Co-Founder of DecoverAI, a legal intelligence platform that helps attorneys uncover insights during investigations and e-discovery. We discussed the biggest gaps in law firm knowledge management today, how AI is transforming investigations and e-discovery, ways that legal professionals can build trust, reliability, and responsible AI practices for high-stakes legal matters, and where the use of Agentic tools in legal is headed.

I spoke with James Barclay, the CEO of Passle, a legal-tech company that supports lawyer-authored thought leadership and helps firms use content for revenue growth. We discussed why cross-selling is important for law firms, how CrossPitch AI differs from traditional KM/experience-management tools, the benefits of integrating laterals and other attorneys into the cross-selling process, and where thought leadership creates the most leverage for cross-selling.

I spoke with Dennis Meador, the Founder and CEO of the Legal Podcast Network. We discussed why podcasting has become a powerful marketing tool for legal professionals, the hallmarks of a successful podcast, and how to overcome the challenges of launching and maintaining a podcast in the legal sector.

In this 50th episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I discussed the prospect of an AI bubble, innovation and client service, and proactively driving change.

I spoke with Matt Lhoumeau, the Co-Founder and CEO of Concord, a contract lifecycle management software platform. We discussed how AI  is changing the way legal teams leverage CLM, the launch of Horizon, Concord's conversational AI platform, why managing contracts manually is still common, and how CLM will evolve.

I spoke with Alex Zilberman, the Co-Founder and CEO of Chamelio, a legal intelligence platform for corporate legal departments. We discussed how AI is changing the way corporate legal teams practice, where they are finding success with AI, where they are still facing challenges, and best practices for driving adoption of new applications.