Where cyber risk is heading in 2026, based on real losses
CISOs are drowning in security data but lack the signals to answer the questions that matter most: where are organizations losing money today, and which controls deliver real ROI? The first session of the Resilience Risk Briefing series examines what current loss data reveals about where cyber risk is headed and which trends actually matter for security and risk leaders.
Host Jud Dressler, Director of Resilience’s Risk Operations Center and a retired U.S. Air Force Colonel, is joined by Andrew Bayers, Director of Threat Intelligence. Together they connect real-world loss experience with frontline threat intelligence, covering today’s loss drivers, the hidden risks that tools and dashboards miss, and the trends Resilience’s threat hunters are tracking now.
The conversation also shows how to turn insurance data into security strategy and provable ROI, with anonymized claims insights and real-world loss narratives on what’s breaking, what’s getting paid out, and why.
About Speakers


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.