The Cyber Insurance Wake-Up Call: What Every Executive Needs to Know Before the Next Claim

About This Webinar

As cyber insurance underwriting requirements grow more stringent and AI-enabled attackers increasingly target mid-market organizations, CEOs, CFOs, CIOs, and COOs face growing pressure to understand their true cyber risk exposure and financial liability.

Many organizations are also discovering that coverage gaps and claim disputes — not just breaches themselves — can create significant business consequences after an incident. This session was designed to bridge that gap with actionable, executive-level intelligence. 

What You'll Walk Away With

Understand the current cyber insurance market:

• What the claims-up/premiums-down paradox means for future rates and coverage availability.
• Learn why mid-market organizations are increasingly targeted by AI-enabled threat actors — and what that means for your risk profile.
• Discover the most common reasons organizations experience coverage gaps, claim denials, or reduced payouts after a cyber incident.
• Know exactly what carriers now require: security controls, approved vendors, MFA, MDM, passwordless, and incident reporting timelines.
• Understand why continuous security posture management is replacing point-in-time compliance — and how to make the shift practical.
• Participate in a live, open Q&A — surface the specific challenges facing your organization and get expert answers in real time. 

Who Should Attend

This session is designed for executive leaders at mid-market organizations who bear responsibility for financial risk, operational continuity, and technology strategy, including CEOs, CFOs, CIOs, COOs, and risk management professionals.

No deep technical background is required. This is an executive-level conversation built for business decision-makers. 

Speakers

• Dr. Robert Becker
  • Principal Consultant, Cybersecurity | DOT Security
• Rusty Abston
  • CIO/CISO | Trawick International
• Stephen Paulin
  • Risk Strategist | Orion Risk Management
• Dan LeCompte
  • Executive Vice President of Sales, West Region | Impact 

Agenda

The session runs approximately 60 minutes and includes an open Q&A portion. Topics will include:

• Current cyber insurance market dynamics: the claims-up/premiums-down paradox and what it signals
• The mid-market threat landscape: how AI-enabled attackers are targeting organizations like yours
• What carriers require today: a detailed look at underwriting expectations and common compliance gaps
• Real-world claims outcomes: case examples of coverage disputes and how they were resolved
• Practical steps to improve resilience, insurability, and executive confidence
• Open Q&A: attendee questions addressed live

Seats are limited. Reserve your spot now and receive the recording even if you can't attend live.

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