Whether it’s migrating to a new cloud environment, rolling out a line-of-business app, or upgrading core infrastructure—the phrase “big IT project” sends shivers through vCSOs everywhere. You plan, budget, validate, and launch. Everyone celebrates. But what most don’t realize until it’s too late is that every change—no matter how well-intentioned—can break something.

You know how this story starts. A breach detonates. The security team locks down the network, scrambles to restore from backup, and works around the clock to piece together what happened. It’s chaos, but it’s controlled chaos—technical, tactical, and familiar. But while the CSO is firefighting, the CFO is walking into something far more destructive: the legal and financial storm that follows.

Cyber insurance might feel like a safety net, but when a breach happens, insurers, regulators, and courts start asking tough questions. Can you prove you followed your cybersecurity policies? Did your team document its compliance efforts? Without airtight evidence, businesses—and their executives—can be accused of negligence, fraud, or worse.