25 Years in Cyber: Lessons from the Frontline with Scott Bailey

In this episode of Beyond the Desk, Underwriting Mini Series, host Sanj Vagad sits down with Scott Bailey, Head of Global Cyber Underwriting at CFC.

Scott looks back on a career spanning 25 years in cyber insurance, from joining Click for Cover (later CFC) as employee number two in 2001, through spells at CNA Hardy and Markel, to his return to CFC three and a half years ago. Along the way, he shares how the cyber market was built from scratch, why the SME protection gap remains so wide, where we are in the current pricing cycle, and why AI is both the biggest emerging threat and one of the industry's best defensive tools.

Whether you're an underwriter, broker or simply curious about how one of insurance's youngest classes of business came to be, this episode is packed with first-hand insight from one of the market's most experienced cyber leaders.

In This Episode You'll Learn

How Scott's career began in car insurance telesales before he joined Click for Cover (later CFC) as employee number two in 2001

What it was like building the cyber insurance product from scratch – before regulation, actuarial data, or even market awareness of the risk existed

The lessons learned moving between an MGA (CFC) and carrier platforms (CNA Hardy, Markel)

Why Scott returned to CFC after a decade away, and the difference between heading global cyber and heading global cyber underwriting

Why only 10–15% of SMEs in developed economies buy cyber insurance, and what the industry needs to do about it

Where we are in the cyber insurance pricing cycle, and why the market may need to firm up in certain geographies

Why AI is both the biggest emerging cyber threat and one of the sector's best defensive tools

Scott's advice for underwriters early in their career, and why curiosity is the most valuable skill in the market