CEO Roundtable: Ari Kaplan on Legal Tech Strategies
The legal technology landscape is rapidly evolving, demanding that general counsel (GCs) and chief legal officers (CLOs) stay ahead of emerging trends and challenges. Legal industry analyst Ari Kaplan recently hosted an inaugural roundtable discussion with leading GCs and CLOs from prominent legal tech companies to reflect on the industry’s current state and explore strategic priorities for the coming year. This article delves into the key insights shared during the roundtable, offering a glimpse into the minds of those shaping the future of legal technology.
Table of contents
The Unique Role of the Legal Tech GC/CLO

Serving as a GC or CLO at a legal technology company presents a unique set of challenges and opportunities. Unlike their counterparts in other industries, these legal leaders often find their roles deeply intertwined with various facets of the company, from product development and governance to data privacy and regulatory compliance. This convergence of legal and business considerations requires a comprehensive understanding of both the legal landscape and the technology driving its evolution.
Colin Levy, General Counsel of Malbek, highlighted this interconnectedness, noting that legal becomes intertwined with various facets of the company. Dennis Garcia, Vice President and General Counsel for Litera, emphasized the opportunity to serve as ambassadors for their companies, using their own products and evangelizing their benefits to other in-house legal teams. This hands-on experience provides valuable insights into customer needs and helps shape product development roadmaps.
Leveraging Internal Expertise and Product Understanding

A significant advantage for GCs/CLOs in legal tech is their deep familiarity with the products their companies offer. Many have extensive experience as users of legal technology, providing them with a unique perspective on customer needs and pain points. This understanding allows them to identify gaps in the market, anticipate future demands, and contribute meaningfully to product development.
Marla Crawford, General Counsel of Cimplifi, pointed out that her extensive background in e-discovery law made her transition to GC of a legal technology company a natural progression. Beth Kallet-Neuman from Relativity echoed this sentiment, emphasizing the unique insight into the customer persona that comes with being both a legal professional and an employee of a legal tech company. This allows for quicker identification of gaps and potential use cases.
Becoming Power Users and Showcasing Value
The roundtable participants emphasized the importance of using their own company’s products to gain a deeper understanding of their capabilities and benefits. By becoming power users, they can identify opportunities to improve the products, develop best practices, and showcase the value proposition to potential customers. This “eat your own dog food” approach fosters credibility and demonstrates a commitment to the solutions they offer.
Jason Barnwell, CLO at Agiloft, discussed plans to run Agiloft’s legal operations on the Agiloft platform, sharing stories and recipes to attract market attention and influence the product roadmap. This virtuous cycle of internal use, feedback, and product refinement ultimately leads to more valuable solutions for customers.
Looking Ahead: Trends and Priorities for 2026
While the roundtable discussion primarily focused on the unique aspects of being a GC/CLO in the legal tech space, it also touched upon broader trends and priorities for the coming year. The rapid advancement of artificial intelligence (AI) was a recurring theme, with participants acknowledging its potential to transform the legal industry while also raising concerns about ethical considerations and data privacy.
The discussion highlighted the need for legal tech companies to prioritize data security, compliance, and responsible AI development. GCs and CLOs will play a crucial role in navigating these complex issues and ensuring that their companies are developing and deploying technology in a way that is both innovative and ethical.
Conclusion
The Ari Kaplan Legal Tech GC/CLO Roundtable provided valuable insights into the challenges and opportunities facing legal technology companies. The unique perspective of GCs and CLOs in this space, coupled with their deep understanding of both legal and technological landscapes, positions them as key drivers of innovation and responsible growth. As the legal tech industry continues to evolve, their expertise will be essential in shaping the future of legal practice.
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