EP. 04 - Cyber Insurance: A False Sense of Security?

Passwork Cybersecurity Webinars

In this episode, host Turpal welcomes cybersecurity architect and Royal Navy veteran Yemi Eniade for an honest exploration of cyber insurance: does it truly protect, or does it lull organizations into complacency? Yemi shares his global experience—from military encryption to banking compliance—and offers practical, real-world insights into how cyber insurance fits into modern risk management.

The discussion covers common misconceptions, regulatory hurdles, the interplay between insurance and technical controls, and how to build policies that actually work. Military analogies, legal perspectives, and hands-on lessons make this an essential listen for CISOs, founders, IT managers, and anyone navigating the complex world of cyber risk.

Key Topics and Time Codes:

• 00:00 – Introduction: Meet Yemi Enyade and his journey from Royal Navy to cybersecurity architect
• 03:16 – What’s to love (and hate) about cybersecurity: The global challenge and daily variety
• 07:18 – Cyber insurance & risk management: How insurance changes investment and security posture
• 11:40 – Safety net or complacency?: Does insurance encourage better controls or just box-ticking?
• 14:48 – What does cyber insurance actually cover?: Legal, compliance, monitoring, and the operational gap
• 19:09 – Making a claim: Lessons from real incidents and why following advice is critical
• 23:03 – Keeping policies up to date: Why simulation and “military-style exercises” matter
• 25:58 – Insurance requirements: Do they drive real improvements or just checklist mentality?
• 29:35 – Should insurers verify security controls?: The case for more active involvement
• 32:23 – Ransomware & negotiation: Does insurance affect willingness to pay or negotiate?
• 35:10 – Does insurance reduce investment in security?: Debunking the myth
• 39:57 – Involving execs, legal, and risk teams: Why buy-in must start from day one
• 44:08 – Insurance in tabletop exercises: Legal and business support, not just technical backup
• 47:45 – The future of the cyber insurance market: Evolving with incidents and claims trends
• 51:49 – Can insurers accurately assess maturity?: Still a black box, and why risk appetite matters
• 55:32 – Designing the ideal policy: What to include, what to leave out
• 58:42 – Does insurance help transparency after a breach?: How QA and sharing lessons improve security

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