2025 Cyber Losses: The Data-Driven Lessons | Resilience Risk Briefing
Resilience’s claims leaders unpack the year’s most instructive cases and what they teach about changing tactics and loss dynamics.
The 2025 cyber claims data, and what it means for 2026
Bad actors don’t need a technical vulnerability to get into a network — they need someone to trust a voice, a message, or a login that looks real. A person manually talking a help desk into a password reset and an AI-generated voice authorizing a wire transfer are different mechanisms aimed at the same target.
Autonomous ransomware kits and AI-generated impersonation just made that approach faster and cheaper to run at scale. Identity, not infrastructure, is now the center of enterprise defense.
Jud Dressler, Director of Resilience’s Risk Operations Center, will moderate a conversation with Stephanie Barnes, Senior Threat Intelligence Analyst at Resilience, and Max Henderson, Managing Director and Global Head of DFIR at Kroll. They’ll cover what’s actually showing up in the threat data right now and how to defend against it.
About Speakers
Jeremy Gittler
Global Head of Claims
Jeremy Gittler, Esq., serves as the Global Head of Claims at Resilience. He is responsible for leading a team that delivers responsive, expert, and solutions-focused support to policyholders facing cyber incidents, as well as lawsuits arising from Technology Errors and Omissions and Media Wrongful Acts. Under his leadership, Resilience continues to build on its reputation as the most trusted, innovative partner in the cyber insurance industry. Prior to joining Resilience, Jeremy held senior leadership roles at AXA XL, where he oversaw both the U.S. Cyber Claims and Underwriting teams. He launched and built the company’s Cyber Claims operations, helping establish AXA XL as a key player in the market. Jeremy began his cyber insurance career at AIG, managing many of the company’s most complex cyber and technology-related claims. Earlier, he practiced litigation at a leading national law firm, where he developed the legal foundation that informs his strategic and pragmatic approach to managing cyber risk. He holds a J.D. from the Benjamin N. Cardozo School of Law and a B.A. from Emory University.
Alex Cutts
Senior Claims & Incident Management Specialist
Alex Cutts is a Senior Claims & Incident Management Specialist at Resilience, bringing 15 years of diverse claims handling experience with four years specializing in cyber incidents. Responsible for day-to-day claims handling throughout the UK and Europe, Alex provides comprehensive end-to-end service with hands-on guidance that helps clients effectively navigate cyber incidents. His unique background includes valuable experience at a computer forensics firm, offering insight into the practical aspects of cybersecurity that enhances his understanding of complex incidents from both insurance and technical perspectives. Alex excels at coordinating effective incident response, ensuring the right experts are engaged at the right time, and guiding clients through each stage of the incident management process. He holds a GIAC Certified Cyber Incident Leader (GCIL) certification.
Judson “Jud” Dressler
Director, Risk Operations Center
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.