How insurers are underwriting AI risk right now
AI is no longer a future risk. It’s a present one, and the gap between emerging threats and reliable financial protection is widening as AI moves from innovation to integration. The question for security and risk leaders is whether their risk management and insurance programs are keeping pace.
Judson Dressler, Director of Resilience’s Risk Operations Center, is joined by Maria Long, Chief Underwriting Officer, and Michelle Worrall, Global Insurance Product Director, to cover the AI-driven exposures to track today, how insurers are evaluating AI maturity and risk data, and a realistic look at market expectations and where critical coverage gaps remain.
About Speakers

Maria Long is the Chief Underwriting Officer at Resilience. With nearly 20 years of experience in the insurance industry, Maria is an established cyber risk manager and underwriter. She has led comprehensive cyber risk programs, enhancing cyber maturity across the policy lifecycle while underwriting Cyber and Tech E&O risks.
Passionate about emerging trends, strategic partnerships, and industry engagement, Maria excels in supporting diverse portfolios, particularly in technology and niche sectors. Known for fostering strong industry relationships, educating stakeholders, and driving strategic initiatives, she combines expertise in communication, leadership, and information privacy and security management to deliver an innovative approach to risk and sustainable portfolio performance.

Michelle Worrall serves as Global Director of Insurance Product for Resilience, a leading global cyber insurer and risk mitigation software provider. Michelle has more than 35 years of collective experience across Cyber, Tech E&O, Media/Entertainment, and Professional Liability insurance, including claims, coverage, underwriting and product development.
Before joining Resilience, Michelle served as Cyber Product Counsel at Coalition and as Assistant Vice President and Cyber Product Specialist at Zurich, North America. Earlier, she co-founded a media liability managing general underwriting agency, which she later sold to an insurer, serving as vice president and media liability product manager. She is an active member of the American Bar Association and holds a Juris Doctorate from University of Kansas School of Law.

Judson Dressler is the Director of the Risk Operations Center. Dressler recently joined Resilience after serving 20 years in the U.S. Air Force. He was previously the Permanent Professor and Head of the Department of Computer and Cyber Sciences at the United States Air Force Academy, where he taught more than 1,200 cadets each year and conducted long-term artificial intelligence and cybersecurity research.
He served as the Commander of the 835th Cyberspace Operations Squadron, where he led 134 cyber airmen to conduct threat-focused, intelligence-driven defensive cyberspace operations. Dressler holds a PhD in Computer Science from Rice University and a Master’s in Computer Science from the U.S. Air Force Institute of Technology.
Any company that sells hardware or software with network connectivity into an EU member state has to report vulnerabilities and incidents affecting that product. The regulation calls these products with digital elements, and it applies to the manufacturer regardless of where the manufacturer is based, so a US firm with no EU presence is covered from the moment its first unit ships into the single market.