Managing threat intelligence for 20,000 companies reveals patterns invisible to most security leaders. Alex Bovicelli, Senior Director of Threat Intelligence at Tokio Marine HCC, sees hundreds of ransomware events monthly, giving him a perspective that challenges industry assumptions about modern threats. The sophisticated attacks making headlines aren't what's devastating smaller organizations. It's groups like Akira Ransomware perfecting SSL VPN brute forcing over years, targeting predictable gaps in authentication controls.

Alex and Ben discuss how cyber insurance shifted from paper applications to technical risk assessment as ransomware as a service exploded, why Alex’s team focuses on native tools and simple configurations rather than threat feeds with obsolete IoCs, and what happens when you alert thousands of companies simultaneously about the same vulnerability. Alex shares his framework for extracting expertise from team members as you lose technical depth in leadership, and emphasizes that emotional intelligence matters more than maintaining hands-on skills.

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[32:39-33:15] I think it is critical for leadership to be very clear in the overall path of the program and the company so that those individual contributors can actually feel like they're participating in a strategic manner. I think the other thing that I find to be an issue that I've noticed is that as an industry we are expecting these kids to get out of school and just have 17 certifications, a master's in whatever, you know, and, we've actually lost touch with the fact that maybe, like, older generations, we understood it was a craft”

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