For many business owners, insurance is something that gets attention once a year—usually when the renewal notice arrives.

But after spending more than 30 years working with family-owned businesses, I've learned that today's risk environment changes far too quickly for an annual check-in to be enough.

That's why I invited Natalie Stone, President of Hill and Stone Insurance Agency, to join me for a recent Ask the CFO session. We discussed the biggest insurance trends affecting businesses today—from cyber threats and employment practices liability to commercial auto claims and the growing importance of proactive risk management.

What became clear throughout our conversation is this: insurance is no longer just about transferring risk. It's about identifying vulnerabilities before they become expensive problems.

Cyber Risk Is No Longer Optional

One of the biggest misconceptions I still encounter is that cyber insurance is only necessary for technology companies.

Natalie made it clear that's simply not true.

If your business uses email, stores customer information, processes payments, or relies on digital systems—which is virtually every business today—you have cyber exposure. Manufacturing companies, professional services firms, healthcare organizations, and family-owned businesses are all targets.

Phishing attacks remain the number one entry point for cybercriminals, and ransomware claims continue to grow in both frequency and severity.

The average ransomware claim now exceeds $1 million. And often, the real cost isn't the ransom itself—it's the operational disruption that follows.

Natalie shared several practical steps every business should be taking:

• Implement multi-factor authentication (MFA)
• Limit access to sensitive information
• Treat cyber insurance applications as risk management checklists
• Invest in a standalone cyber policy rather than relying on basic endorsements
• Ensure funds transfer fraud coverage is included

Too many businesses assume they're protected, only to discover critical exclusions after a claim occurs.

AI Is Making Fraud More Sophisticated

One area that particularly caught my attention was the growing threat of funds transfer fraud.

With advancements in AI, cybercriminals can now clone voices, impersonate executives, and create convincing email requests that look legitimate.

As someone who has spent decades in CFO roles, I can tell you these scams are real.

I've seen firsthand how employees can feel pressured to act quickly when they believe a request is coming from leadership.

Technology helps, but process matters just as much.

Every business should have clear verification procedures for financial transactions, including:

• Multiple approval levels for large payments
• Phone verification using known contact information
• Automated payment processes where possible
• Regular employee training on social engineering risks

Once funds are transferred incorrectly, recovering them can be incredibly difficult.

There Is Some Good News on Insurance Costs

After several years of challenging renewals and rising premiums, we're finally seeing some positive movement.

According to Natalie, the property and casualty market is beginning to soften, creating more favorable conditions for buyers. Supply chain disruptions and inflationary pressures have eased, helping stabilize costs.

That said, not every category is improving.

Commercial auto insurance remains a significant challenge because claim severity continues to rise. While accidents may be happening less frequently, settlements involving bodily injury, pain and suffering, and other non-economic damages are increasing.

Cyber insurance pricing also continues to vary widely depending on industry, growth, and security controls.

My advice: don't assume your renewal is your only option. Review your coverage annually and make sure you're exploring alternatives.

The Risks Inside Your Business May Be Growing

When most business owners think about insurance claims, they picture property damage or workplace injuries.

Increasingly, some of the largest claims involve employees.

Natalie highlighted employment practices liability as one of the most overlooked areas of risk today. Discrimination, harassment, wrongful termination, and retaliation claims are becoming more common—and more expensive.

An aging workforce, changing workplace expectations, and evolving social norms are creating new challenges for employers.

At the same time, what the insurance industry calls "social inflation" is driving larger jury awards and settlements.

Every business owner should understand whether they have adequate:

• Employment practices liability insurance (EPLI)
• Directors and officers (D&O) coverage
• Workplace policies and training programs

Even organizations with great cultures can face significant claims.

Workers' Compensation Is a Bright Spot

Not every trend is negative.

Workers' compensation remains one of the strongest-performing areas of the insurance market.

Improved safety protocols and a greater focus on employee wellbeing have reduced claim frequency over time.

However, there's an important detail many growing businesses overlook.

If you employ remote workers in multiple states, your workers' compensation policy must reflect those locations.

As companies expand geographically, coverage gaps can emerge quickly if insurance policies aren't updated accordingly.

Fast-growing businesses need to pay particular attention here.

Your Insurance Broker Should Be More Than a Vendor

Throughout my career, I've learned that the best external partners don't just provide a service—they become trusted advisors.

Insurance should work the same way.

A strong insurance broker takes the time to understand your business, your growth plans, and the risks unique to your operations. They help you think proactively rather than reactively.

That means having conversations about:

• Expansion plans
• New locations
• Acquisitions
• Changes in operations
• Workforce growth
• Emerging risks

The more transparent you are, the better your advisor can help protect your business.

At the end of the day, insurance isn't just about policies and premiums.

It's about preserving the value you've built.

For family-owned businesses especially, managing risk well protects not only the company, but also the employees, customers, and families who depend on it.

Because the businesses that thrive long term aren't simply the ones that buy insurance.

They're the ones that actively manage risk before problems arise.