AI from the Inside
65 min|April 6, 2026
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AI from the Inside

An interview with Michael A. Gerstenzang

The integration of artificial intelligence into the legal profession presents a pivotal tension between traditional practices and technological advancement. This issue is of profound importance as it challenges the long-standing operational models of law firms and compels a reevaluation of how legal services are delivered. Michael Gerstenzang, the senior partner of Cleary Gottlieb and former managing partner, brings his unique insights to this discussion. As an AI optimist, Gerstenzang has spearheaded transformative initiatives within his firm, notably the acquisition of an AI startup, Springbok AI, and the establishment of ClearyX, an innovative technology services business. Through these efforts, Gerstenzang explores the potential of AI to fundamentally alter legal practice, offering a glimpse into a future where law firms not only adapt but thrive amidst technological change.

Gerstenzang addresses the transformation of due diligence processes in M&A transactions through AI. Historically, this labor-intensive task was conducted by junior associates at high costs, a model that does not appeal to all clients. Gerstenzang and Cleary's response was the creation of ClearyX, an affiliate focused on utilizing technology to streamline due diligence. The successful implementation of ClearyX demonstrates a willingness of even elite firms to leveraging AI in response to client demand and highlights the potential for AI to reshape traditional billing models. 

Cleary, under Gerstenzang's leadership, didn't stop there: Michael explains the strategic acquisition of Springbok AI, which serves as Cleary Gottlieb's AI acceleration team. This move underscores the importance of having in-house technological capability to develop bespoke solutions tailored to specific client needs. While off-the-shelf products from major tech companies remain the dominant source of tech, Gerstenzang emphasizes the necessity of customizing some tools to bridge gaps and meet immediate client demands. The acquisition exemplifies a forward-thinking approach that is unique among top global firms.

More broadly, Gerstenzang speaks to the increasing need for greater collaboration between lawyers and technologists to enhance service delivery and client satisfaction. According to Gerstenzang, this shift necessitates a cultural change within law firms, where technologists are viewed as integral partners rather than support staff. He shares how the collaboration between ClearyX, the AI acceleration team, and traditional legal practices at Cleary Gottlieb offer one path towards maintaining a competitive edge during this tech transition.

Michael Gerstenzang is the senior partner at Cleary Gottlieb, where he leads initiatives in AI integration and technological advancement. With a focus on innovative practices and client-centered solutions, Gerstenzang's work positions Cleary Gottlieb as a leader in the evolving landscape of legal services.

Additional Resources

No specific legal authorities were cited in this discussion.

New Law Order

This episode is part of our New Law Order podcast. Explore more from the series ›

About Michael A. Gerstenzang

“The future of law firms will be shaped as much by how they operate as by what they practice.”
Michael Gerstenzang is the senior lawyer and long time managing partner of Cleary Gottlieb Steen & Hamilton LLP, where he oversaw global strategy, talent development, and firm operations. Drawing on decades of experience in leadership and litigation, he focuses on how evolving client demands, technology, and changing talent models are reshaping the modern law firm. His work explores the future of firm structure, leadership, and the competitive pressures transforming the legal industry.