May 6, 2025

Does Your Business Need a Cyber Risk Assessment?

Cyberattacks are no longer isolated to large corporations with massive data troves — they’re now a daily threat to businesses of all sizes. In the third quarter of 2024 alone, over 422 million data records were exposed, affecting millions of individuals and organizations worldwide, according to Statista. 

Whether you’re a small business or a growing enterprise, understanding your digital vulnerabilities is essential. A cyber risk assessment is a proactive step that strengthens your security posture and aligns directly with securing cyber liability insurance.

What Is a Cyber Risk Assessment?

A cyber risk assessment is a structured review of your organization’s digital infrastructure. It helps you identify where sensitive data lives, who has access to it, and how it’s protected — or vulnerable. Many business owners are surprised to discover how exposed they really are.

Even if you don’t handle financial transactions or store medical records, your company still likely holds employee data, client contact information, and login credentials. Without a formal risk assessment, these vulnerabilities often go unnoticed until after an attack.

By identifying gaps in your network security, employee training, and third-party vendor management, a cyber risk assessment becomes the foundation of your cybersecurity planning. It’s a proactive way to reduce risk and strengthen your company’s defenses.

What Is Cyber Liability Insurance and Why Is It Critical?

So, what is cyber insurance, exactly? Cyber liability insurance helps cover the financial losses associated with cyberattacks and data breaches. This often includes:

  • Costs to investigate and respond to a breach
  • Legal fees and regulatory fines
  • Notification costs to inform affected customers
  • Business interruption losses
  • Ransomware payments and negotiation support
  • Public relations and reputation management

Oakwood Risk works closely with businesses to ensure their cyber liability policies reflect real-world risks and provide the protection they need to recover quickly after an incident.

Signs Your Business Might Be at Risk

You don’t have to be a tech company to be a target. Common red flags that indicate your business could be vulnerable include:

  • No in-house IT support or reliance on outdated systems
  • A remote workforce with unsecured devices
  • Collection or storage of customer or payment data
  • No formal cybersecurity training for staff
  • Use of third-party vendors without security oversight

A cyber risk assessment can uncover these issues and prioritize actions to fix them. It’s a smart move whether you’re a startup or a well-established organization.

Cyber Risk Assessments as a Foundation for Insurance

Insurance providers are increasingly looking for evidence that a business has taken proactive cybersecurity measures. A completed risk assessment shows you take data protection seriously — and it can also improve your insurance eligibility.

In fact, having a documented cybersecurity strategy may lead to more favorable policy terms and lower premiums. It’s a win-win: You reduce your exposure to cyber threats and strengthen your position when applying for coverage.

Taking the Next Step: How Oakwood Can Help

Cyber threats are evolving rapidly, but that doesn’t mean your business has to be vulnerable. Oakwood Risk takes a consultative approach to protection, helping clients assess risks, choose the right insurance products, and plan for long-term resilience. You can read how other businesses have benefited from our guidance on our testimonials page.

Don’t wait for a breach to expose your vulnerabilities. Contact Oakwood Risk to schedule a cyber risk assessment and explore cyber liability insurance options tailored to your business.

Oakwood Risk

Oakwood Risk provides industry-leading insurance services, solutions, and counsel to our clients. Our professionals are valued for their ability to provide outstanding customer service, with a commitment to the relentless pursuit of value-added solutions, results, and comprehensive coverage.

Oakwood Risk at Work

One of our clients had been purchasing D&O insurance from the same carrier for several years. We looked at their tower and realized that not only was their primary carrier not A+ rated, they were also paying too much for the primary layer. We were able to move the coverage to A+ rated paper and save the client six figures.