The $2.3M Mistake Hiding in Your Cyber Policy
Overview
Four expert-led webinars. Real-world cyber risk, SOC strategy, AI governance, and vendor risk—plus live Q&A and take-home playbooks.
Summer 2026 Cyber Webinar Series is a four-part, 30-minute webinar series for mid-market leaders who need practical answers on the topics boards, insurers, and regulators are asking about right now: cyber insurance readiness, Managed SOC / detection, AI governance, and third-party vendor risk.
Each session is designed to be fast, tactical, and immediately usable. Less theory, more here's what to do next.
What to Expect If You Attend
Four concise sessions (30 minutes each) with time-boxed, real-world content and live Q&A
Working frameworks and checklists you can bring to leadership, audits, renewals, or vendor reviews
Examples and teardowns (denied claims, detection failures, Shadow AI sprawl, vendor breach cascades) to show what good looks like in 2026
Recordings + slides delivered after each session (attend live for Q&A and the attendee bonus offers)
Series Format
0:00-5:00 Welcome + why the topic matters now
5:00-25:00 Practical content (frameworks, examples, and playbooks)
25:00-30:00 Live Q&A + next steps
Who Should Attend
Built for CEOs, CIOs, CISOs, IT Directors, GRC Leads, and General Counsel. If you own risk, security operations, compliance, renewal readiness, or vendor oversight this series will help you tighten your program without adding noise.
AGENDA
Mike O'Connor, VP, Brown & Brown, Christopher Yula, VP of Sales & Strategy, CyberSecOp
In 2024, a mid-market manufacturer attested to MFA compliance on its cyber renewal — and watched a $2.3M ransomware claim get denied over one missed VPN account. This is no longer the exception. Coalition data shows 82% of denied cyber claims involved organizations without fully implemented MFA, and 41% of applications are now rejected on first submission. Carriers have moved from questionnaire-based to evidence-based underwriting, and the gap between what executives think they bought and what their policy will actually pay is the largest it has ever been.
Join CyberSecOp and Brown & Brown for a focused 30-minute session where we break down real denied claims, expose the hidden gaps in 2026 policies covering AI, social engineering, and nation-state exclusions, and give you the seven evidence checkpoints your carrier will require at renewal. You will leave knowing exactly whether your policy will pay when it matters most.