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Treat insurance as an ongoing leadership and operations issue

RCSI Rich Carroll APR 2026
May 4, 2026 at 12:30 p.m.

RCS Influencer Rich Carroll says that when facing the volatile insurance market, it's important to stay close to your broker, stay connected to your peers and stay focused on the controllable parts of your business.

From my perspective as a consultant and former contractor, the smartest contractors are going to treat insurance as an ongoing leadership and operations issue, not just an administrative expense. That starts with engaging your broker often, ideally monthly, instead of waiting until renewal season to have the conversation. Contractors should be asking what trends the broker is seeing, what underwriters are focusing on, where claims are coming from and what actions can improve their position over time. Frequent communication gives a company a chance to be proactive instead of reactive. 

I also think there is real value in talking with other contractors, especially through peer groups or industry networks. Many roofing contractors are dealing with the same challenges, and there is a lot to learn from what others are seeing in the market. Whether it is fleet issues, claims trends, safety programs, deductibles or coverage changes, peer conversations can help contractors understand what is happening and where they may need to adjust. Sometimes the best ideas come from hearing how another contractor is managing the same pressure. 

Internally, leaders should also create more accountability around the things they can control. That includes jobsite safety, driver performance, incident reporting, training and claims follow-up. Reviewing claims history regularly, tracking trends and holding managers accountable for preventable losses can make a real difference over time. The companies that do this well will be in a better position when underwriters evaluate them. 

Finally, contractors have to make sure rising insurance costs are being considered in pricing and overall business planning. Too many companies absorb these increases without changing how they estimate work, and that puts even more pressure on margins. 

The insurance market may be volatile, but roofing contractors are not powerless. The best response is strong leadership, frequent communication with trusted advisors and learning from others in the industry who are facing the same challenges. 

The bottom line is this: don’t just shop insurance once a year and hope for the best. Stay close to your broker, stay connected to your peers and stay focused on the controllable parts of your business. That is where contractors can create an advantage, even in a difficult market. 

Rich Caroll is a business owner in the roofing industry. Read his full bio here.


Rich Carroll is the owner of Carroll Consulting Group. Read his full bio here.


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