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608-571-5345 Derek@wolfofpropertycasualty.com
Service Overview
Derek founded the Cyber Liability division at a top 50 insurance broker and was responsible for over $40M in annual cyber liability placements. He has conducted over 200 tabletop exercise for companies of all industries. In today’s threat landscape, cyber incidents aren’t a question of if they’re a question of when. I lead high-impact cyber liability simulations and tabletop exercises designed to pressure test your organization’s readiness, expose hidden vulnerabilities, and strengthen coordination between leadership, IT, legal, and risk management.
These sessions replicate real world attack scenarios ransomware, data breaches, wire fraud, system outages, regulatory escalations and guide your team through the technical, financial, and communication decisions required at every stage.
The outcome? A clear, actionable roadmap to improve your cyber resilience, tighten response protocols, and ensure your insurance coverage, limits, and vendors align with the realities of modern cyber risk.
Practical. Realistic. Unfiltered.
Exactly what today’s organizations need to stay ahead of the threats they can’t afford to ignore.
- Realistic attack scenarios tailored to your industry, systems, and risk profile.
- Step-by-step incident walkthroughs covering detection, containment, communication, and recovery.
- Decision-point challenges that pressure-test leadership, IT, legal, HR, and vendor coordination.
- Role clarity exercises defining who owns what before and during a real incident.
- Insurance alignment review to ensure coverage, limits, and obligations match actual exposure.
- Regulatory and notification mapping for data breaches, privacy events, and compliance triggers.
- Financial impact modeling to project downtime, business interruption, and reputational risk.
- After-action report & roadmap detailing gaps, strengths, and immediate improvement priorities.
