Roman Itskovich on What Businesses Get Wrong About Cyber Risk

Roman Itskovich, Co-founder & CRO at At-Bay, joins Mudassar Malik on Behind the Growth to unpack how cyber risk has evolved into a primary business risk—and why traditional approaches to managing it are no longer sufficient. Roman traces his path from military and fintech into cyber, highlighting how increasing reliance on technology has shifted risk from the periphery to the core of enterprise operations. 

He explains why cyber risk behaves differently from other forms of risk. Unlike static business risks, technology environments are constantly changing, and so is the level of exposure. That shift requires a fundamentally different approach—one that goes deeper than surface-level indicators like industry or revenue, and instead focuses on understanding the underlying technology stack in detail. 

Roman introduces At-Bay’s “insure-sec” model, which combines insurance with active security. Rather than simply underwriting risk based on limited inputs, this model continuously evaluates and improves a company’s security posture. He breaks down the two principles behind this approach: the need for technical visibility to assess risk accurately, and the ability to actively intervene to reduce that risk over time. 

The conversation highlights how this model changes the role of insurance—from a static transfer of risk to a more dynamic system that informs better decisions. For enterprise leaders, it reframes how to think about cyber risk, not just as something to mitigate, but as something that can be measured, managed, and priced with greater precision. 

Roman covers topics like: 
- Cyber risk as business risk  
- Technology stack risk visibility  
- Insurance and security convergence  
- Dynamic vs static risk models  
- Underwriting beyond surface metrics 

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