In this episode of Making Risk Flow, host Jake Harding speaks with Ross Wirth, Head of Strategic Tech Ecosystem at CyberCube, about why cyber insurance requires a new playbook for risk assessment. Ross explains how traditional underwriting struggles to keep pace with dynamic security environments, and why real-time data visibility is now essential for identifying concentration risk, single points of failure, and systemic exposures like cloud outages. 

The conversation explores shifting from static applications to continuous monitoring, balancing AI-driven insights with human judgment, and designing underwriting strategies that prioritise prevention over post-incident repair. Whether you're an underwriter, broker, or cyber risk leader, this episode offers practical guidance on using data intelligently while preserving the relationship-driven core of insurance.

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Our previous guests include: Bronek Masojada of PPL, Craig Knightly of Inigo, Andrew Horton of QBE Insurance, Simon McGinn of Allianz, Stephane Flaquet of Hiscox, Matthew Grant of InsTech, Paul Brand of Convex, Paolo Cuomo of Gallagher Re, and Thierry Daucourt of AXA.

Check out the three most downloaded episodes:

• The Five Pillars of Data Analytics Strategy in Insurance | Craig Knightly, Inigo
• 20 Years as CEO of Hiscox: Personal Reflections and the Evolution of PPL | Bronek Masojada
• Implementing ESG in the Insurance and Underwriting Space | Simon Tighe, Chaucer, and Paul McCarney, Moody's