There’s a dangerous assumption lurking inside many boardrooms today: If nothing bad has happened, nothing bad is coming. For vCSOs, that’s the most perilous mindset you can allow your clients to fall into. And it happens faster than you think. If you’re not actively telling the story of the risks you’re managing, the value you’re delivering, and the dangers you’re helping your clients avoid, you’ll wake up one day to find your budgets slashed and your influence gone. 

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. 

Insurance providers aren’t just selling policies anymore. They’re selling security solutions, acting as MSSPs, and compliance auditors. They’re bundling cybersecurity tools into their policies, dictating security frameworks that serve their own financial interests, and pushing businesses toward insurer-managed security stacks that remove independent oversight. This is not about protecting businesses. It’s about minimizing their own liability. 

In today’s threat landscape, where cybercrime losses exceed $10 billion annually, the situation has reached unprecedented urgency. If your organization isn’t already prioritizing evidence collection, you’re leaving the door wide open to financial ruin, reputational collapse, and legal disaster. 

Cyberattacks don’t just target data—they shatter trust, disrupt operations, and tarnish reputations. As a vCSO, engaging a third-party penetration testing provider isn’t just about compliance; it’s about staying ahead of the hackers, protecting customer relationships, and demonstrating that security is a top priority.

Choosing the right KPIs allows CSOs to strategically align security initiatives with business objectives, ensuring that every aspect of the security program not only supports but enhances business operations.

As hackers grow more sophisticated, you can no longer afford to simply keep doing the same things over and over again. Trust me when I say that the hackers certainly aren’t!