As a vCSO, this is your moment of truth. Because compliance isn’t about checking a regulatory box. It’s about proving the organization wasn’t negligent. And if your client’s security decisions aren’t mapped to a recognized standard, you’re not building a defense—you’re handing ammunition to regulators, insurers, and attorneys. 

Most executives assume that once an employee is hired, they know the rules. They assume policies are read and understood. They assume common sense prevails. But assumptions don’t hold up in court. When a breach happens, you’ll be asked for proof. Proof that users were trained. Proof that they acknowledged the risks. Proof that they understood their responsibilities. If you can’t produce that evidence, it’s your neck on the line. 

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.