What’s Missing from the Trucking Insurance Conversation

Last month, I traveled to Dallas for Women in Trucking’s 2025 "Accelerate!" conference. I wanted to get a first-hand look at the trucking industry and its approach to risk management. Being relatively new to both insurance and trucking, I wasn’t sure what to expect.

I was immediately struck by the energy. Walking into the kickoff speech on Monday morning, I was greeted by over a thousand women wearing red, a symbol of empowerment. That set the tone for the next three days. I spent my time exploring the exhibit hall and, more importantly, just listening to people: fleet safety managers, risk managers, technology providers, insurance professionals, and drivers on the front lines.

Since then, I’ve been reflecting on this experience and speaking with the rest of the Luzern team about it. Here are six observations from my time on the ground in Dallas.

1. Trucking companies are facing serious challenges.

It didn't take long to realize the pressure this industry is under. In almost every conversation I had, certain themes were common. I heard about the anxiety surrounding nuclear verdicts (jury awards over $10 million) and the rise of lawsuit abuse. Combined with general economic drags and the struggle for driver retention, it is clear that leading a trucking company today takes resilience and creativity.

The educational sessions underscored how complex the environment has become. On the technology side, I learned about emerging risks in cyber, tech liability, and data privacy. Regulations are also shifting in many areas, including cannabis, hazmat, and pharmaceuticals.

2. There is a ton of investment in safety programs and technology.

The commitment to safety I witnessed was inspiring. The exhibition floor was packed with vendors selling telematics, AI driver recruitment solutions, and compliance software. Almost every session touched on safety improvements in some way.

Many motor carriers are making safety innovation a high priority. They are spending millions of dollars on training and technology. Their reasons include doing right by their drivers and the public, improving loss ratios, furthering innovation, and building competitive advantage.

I met professionals deeply proud of their safety cultures, and the better outcomes they’re achieving as a result for their fleets and clients.

3. Insurance premiums are rising anyway.

This was the most painful disconnect I observed. I heard from companies taking the steps within their power to protect their operations. They’ve implemented the tech, improved their safety scores, and reduced accidents. They deliver better-than-market loss performance, an accomplishment that should be rewarded. Yet, when renewal time comes, their insurance premiums are still going up.

It feels like a punishment for good behavior. Commercial insurers are losing money on trucking accounts year after year. As they feel the squeeze, they’re raising rates and restricting capacity. This can impact all customers regardless of individual performance. It was a frustration I heard voiced again and again.

4. Captive insurance may be the missing solution, but it was surprisingly absent from the discussion.

Given the frustration regarding premiums, I expected to hear a lot of buzz about alternative ways to finance risk. To my surprise, almost no one was talking about captive insurance.

For those who don't know, a captive is essentially an insurance company your business owns. A captive allows you to write your own coverage, structure the pricing to accurately reflect your performance, and capture the underwriting profits. Over time as the surplus grows, your captive builds as a strategic asset. It’s an alternative approach than simply paying for coverage in the traditional market. 

This seemed like a potential solution to some of the problems people were describing. 95% of the Fortune 500 use captives for a reason, and that includes the largest transportation and logistics companies. But as far as I’m aware, I was the only person at “Accelerate!” proactively bringing up captive insurance. There’s a gap between the problems mid-market firms are facing and the solutions being discussed.

5. There seem to be a lot of trucking companies that would be good fits for a captive.

Since the concept wasn’t prominent at the conference in Dallas, I wanted to share a few "back of the napkin" metrics. While you need a proper assessment to be sure, you might be a candidate for a captive if your company:

• Operates over 25 units.
• Spends over $1 million in annual premiums (often combining Auto and Workers' Comp).
• Has a predictable loss history supported by good data.
• Is committed to risk management (which, based on this conference, applies to many of you).

If you check those boxes, you might be able to stop renting your insurance and start owning it. To head off a common misconception, a captive doesn’t mean retaining all your risk. You choose how much to retain, and starting small is a great approach.

6. I’ll be out on the road again soon to keep exploring these points.

I learned so much in Dallas, but I know I’ve only scratched the surface. I’m planning to attend more trucking conferences in the first half of next year to keep learning and to keep sharing the message that there is an alternative to the traditional insurance market that rewards you for well-managed risks.

If you’re planning on being at the following events, drop by our booth, get in touch on LinkedIn, or shoot me an email. I’d love to hear your story.

• LINK Retail Supply Chain conference (February 1-4 in Orlando, FL)
• Manifest, presented by DHL (February 9-11 in Las Vegas, NV)
• TCA’s Truckload 2026 (February 28-March 3 in Kissimmee, FL)
• Final Mile Forum (February 18-20 in Austin, TX).

In the meantime, if you're curious about whether a captive could work for your business, we're here to answer your questions.

Get a Captive Readiness Snapshot

Want a clear assessment using your actual numbers? We offer a short working session followed by a concise executive summary. It shows whether a captive could realistically fit your operation and where it might make sense to start. Get in touch and let's talk.