Caroline McCaffery leads Outside GC’s Artificial Intelligence, Cybersecurity & Privacy practice, advising technology startups and growth companies on matters ranging from corporate transactions and commercial agreements to AI governance, privacy, cybersecurity, and emerging technology risk.

She has worked with technology companies since 2000, first as a corporate and securities lawyer and later as a General Counsel, business executive and technology founder. Her corporate practice spans the startup lifecycle, including formation and governance, complex equity and debt financings, cap table management, mergers and acquisitions, commercial contracting, and day-to-day strategic counseling. That experience informs her approach to emerging technology by connecting legal requirements to a company’s product, business model, and operational realities.

Caroline began working with artificial intelligence in 2015 as General Counsel of Clarifai, an AI computer vision company. At a time when relatively few lawyers were focused on AI-specific legal issues, she advised on AI licensing, intellectual property and model rights, data use, privacy, cybersecurity, and early AI ethics and governance. Her role later expanded to include Finance, People, and Information Security, giving her a broader operational perspective on technology and risk.

She also co-founded her own AI technology startup, where she designed and developed AI-enabled technology for legal, security, compliance and third-party risk workflows.

Today, Caroline brings her practical experience and legal acumen together for Outside GC clients, helping them implement and govern AI and translate evolving legal requirements into practical policies and controls, while continuing to advise on the corporate and commercial matters that arise throughout a startup’s lifecycle.

Caroline began her legal career at Gunderson Dettmer LLP. She is admitted in New York and California holds CIPP and AIGP certifications. She earned her J.D. from NYU School of Law and her undergraduate degree from the University of Pennsylvania.

Caroline lives just north of New York with her family. A favorite fun fact is that she was on the Penn ski team.