Andrew Woolf

Chief Strategy and Innovation Officer

Recent Publication:

What One Big Law firm is Doing to Eliminate 'AI Pilot Fatigue'

Andrew Woolf was quoted in a Business Insider article discussing how law firms are addressing “AI pilot fatigue” amid the rapid growth of legal technology offerings.

Andrew Woolf is the chief strategy and innovation officer at Cozen O'Connor, where he works closely with the firm's executive leadership to define and execute the firm's long-term strategy, focusing on growth, operational transformation, and artificial intelligence.

Andrew's work sits at the intersection of strategy, operations, and technology. He is responsible for translating firm strategy and advances in AI into execution — embedding AI into legal and business workflows, strengthening the firm’s knowledge and data infrastructure, and evolving how legal services are delivered to clients.

His background spans legal practice, federal government service, and operating leadership. Andrew began his career clerking in the federal courts and practicing at a leading Am Law 100 firm, where he advised on complex mergers and acquisitions, hostile takeovers, and high-stakes corporate disputes. He later served as senior advisor to the deputy secretary and under secretary at the U.S. Department of the Treasury, focusing on economic policy, innovation, and organizational strategy.

He subsequently held senior roles at high-growth technology companies in New York and Philadelphia, where he led strategy, operations, and business transformation efforts.

Andrew earned his B.A. from Williams College and his J.D. from Yale Law School, where he served as a managing editor of the Yale Law Journal. He is admitted to practice in New York.

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Experience

Publications

What One Big Law firm is Doing to Eliminate 'AI Pilot Fatigue'

April 27, 2026

Andrew Woolf was quoted in a Business Insider article discussing how law firms are addressing “AI pilot fatigue” amid the rapid growth of legal technology offerings.

Education

  • Yale Law School, J.D., 2005
  • Williams College, B.A., 2002

Honorable Judge Jed S. Rakoff of the U.S. District Court for the Southern District of New York, 2005-2006

Honorable Judge Wilfred Feinberg of the U.S. Court of Appeals for the Second Circuit, 2006-2007