More than 20 years ago, a group of commercial roofing contractors challenged the traditional approach to insurance. They came together to create a captive that would give them greater control over how they financed and managed risk. The concept of a group captive itself was not new, but what followed was a complete transformation of how these businesses operated.
In time, Roofers Insurance Ltd. evolved into much more than an insurance structure. It became a dynamic forum where contractors shared ideas; challenged one another; learned from one another’s operational experiences; and worked collectively to improve safety, operations and business performance. Supported by experienced partners who shared a long-term commitment to the roofing industry, the captive created an environment where collaboration became just as valuable as coverage.
Throughout the years, members discovered RIL wasn’t simply changing how they financed risk—it was changing how they led their businesses. As one of the longest-standing and most specialized roofing group captives, RIL is proof shared accountability creates stronger businesses, safer workplaces and a more resilient roofing industry.
A different way to think
For many businesses, insurance is little more than a transaction. Coverage is purchased; premiums are paid; and the hope is a claim never occurs. With this model, risk is often viewed as a cost to be financed rather than a discipline to be actively managed. The captive model turns that thinking on its head, giving members a financial and operational stake in the outcomes they help create where success is measured not only by premium costs but also by how effectively members control losses, strengthen risk control standards and contribute to the overall health of the group.
This means contractors no longer need to manage risk in isolation; they become part of a community where every member shares responsibility to uphold high standards of safety, operational excellence and accountability. For members, this shift creates a different level of ownership.
According to Paul Tomczuk, captive president and president of R.H. Marcon Inc., State College, Pa., RIL gives contractors a more active role in managing outcomes rather than simply reacting to market changes.
“It’s managing risk, and it’s managing costs,” Tomczuk explains. “At the end of the day, if you are going to be a successful commercial roofing company, it is extremely difficult to absorb large premium increases. In the traditional market, you are at the mercy of industry-wide loss trends and carrier appetites, but in a successful group captive, you have much more control over what you pay in premiums.”
This ownership mindset has empowered members to take on more responsibility and adopt a more strategic mindset to risk management.
Sustaining a strong captive also means sustaining a strong profession and nurturing the next generation of leaders who will carry the industry forward
More than a captive
Although traditional business wisdom advises keeping market rivals at arm’s length, RIL chose a different path. RIL members recognized the sustained health of the captive depended not on the size of the companies but on the caliber of their leadership.
As Gary Houck, captive strategic director and chairman of Houck Group Inc., Harrisburg, Pa., recalls: “Some of the people I invited were my closest competitors. But they were good competitors. They were people of integrity.”
That early emphasis on character over market share established a foundation of trust that transformed competitors into collaborative partners. Over time, relationships evolved and discussions moved well beyond the topic of insurance. Members began sharing operational ideas, exchanging lessons learned and helping one another solve business challenges during RIL’s semiannual workshops. The workshops are not passive governance meetings. They are active, hands-on working sessions where competitors dissect claims, analyze safety protocols and share operational strategies.
Between workshops, conversations continued through a shared member portal, creating a year-round exchange of knowledge, experience and best practices. Rather than navigating challenges alone, members have access to a trusted network of peers who are invested in one another’s success.
The collaboration between members doesn’t just build community; it yields tangible business outcomes.
“After seeing similarly sized companies within the captive invest in dedicated safety leadership, our team decided to bring on a full-time safety director, which has been a real game changer for us. It was more than just a single hire. It reinforced the concept that safety is a shared responsibility across our entire organization,” Tomczuk says.
The culture of collaboration, expertise and shared values RIL has become known for are the same reasons so many members have remained with the captive. In fact, 75% of RIL members have been part of the captive for more than a decade. It is also what has led to RIL’s continued expansion from 19 founding businesses in 2006 to 195 active members representing more than 38 states.
Understanding captives
A member-owned group captive is an insurance company formed and controlled by multiple organizations to insure certain risks for the member companies. The group captives are wholly owned and controlled by the member companies, and they only insure the member companies that own the captive.
Unlike single-parent captives, which are typically viable for large, well-capitalized companies, the group captive structure allows small- and mid-sized companies to enjoy many of the same benefits of captive insurance by combining resources and sharing risk with other like-minded organizations.
Although members own and control the captive, they typically use a captive management company to oversee day-to-day operations, including governance, regulatory reporting, cash management and accounting, audit and tax coordination, and corporate secretarial functions. The captive also contracts with industry service professionals and third-party administrators to provide services such as claims management, loss control, policy issuance, reinsurance and actuarial services. Ultimately, the captive’s board of directors, composed of representatives from the member companies, serves as the final decision-making authority.
Considering a captive?
Although every captive is structured differently, successful group captives often begin with organizations that share similar values, risk profiles and a commitment to long-term accountability. Early challenges typically include building trust among participants, establishing governance structures, securing adequate capital and maintaining alignment around shared risk management goals.
For contractors interested in exploring a captive solution, the process generally begins with evaluating member interest, identifying like-minded organizations, engaging experienced captive advisers and conducting a feasibility study. Captive costs, capital requirements and organizational structures vary significantly. Contractors should consult their broker representative and trusted captive professionals to determine whether a captive arrangement is appropriate for their business.
According to the National Association of Insurance Commissioners, captive insurance companies have been in existence for more than 100 years. The term “captive insurance” was coined by Frederic Reiss, a property-protection engineer in Youngstown, Ohio, in 1955. Reiss established the first captive insurance company in Bermuda in 1962. During the past 30 years, there has been significant growth in the captive market. Now, there are about 8,000 captives globally compared with about 1,000 in 1980, according to Oldwick, N.J.-based AM Best Captive Center, an independent, third-party credit ratings resource.
An aligned partnership
Although committed members are the heartbeat of a successful captive, the model cannot succeed in isolation.
The success of any group captive program is built on strong collaboration between the carrier, broker, service providers and member companies. For example, CNA values all its broker relationships and views them as an integral part of the captive experience, providing ongoing guidance to their clients while working closely with the carrier to identify emerging loss trends and opportunities for education and risk improvement. Equally important is the selection of service providers, such as a captive consultant with deep construction expertise, as contractors face a far more complex set of casualty exposures that require specialized claim adjustment, proactive risk management and industry-specific vendor support that focuses on fleet safety and contractual risk transfer.
Captive Resources, a consultant to captive insurance groups based in Itasca, Ill., believes vendor alignment is one of the defining reasons RIL has remained successful.
John Rozwat, senior vice president of Captive Resources and captive executive for RIL, explains the captive’s unique structure means success “isn’t dependent on a single organization; it’s the result of a highly collaborative partnership among the members, the captive consultant, the carrier, the third-party claims administrator, actuary, auditors, legal counsel and the insurance brokers.”
Each brings specialized expertise, “while remaining aligned around the same long-term objectives: improving safety, lowering the total cost of risk, achieving long-term financial stability and creating sustainable value through active member governance.”
CNA, RIL’s underwriter, also is deeply involved with the management of RIL. CNA has maintained a consistent underwriting philosophy that has allowed the captive to make thoughtful, strategic decisions even through changing market cycles. CNA has engaged with all RIL members to share expertise about enhancing safety and risk management practices. For RIL, CNA provides insurance coverage for lead umbrella, property, marine, professional liability, errors & omissions and pollution. And CNA has a dedicated group of construction captive professionals to underwrite, service and administer RIL policies and deliver specialized, tailored member support.
Rozwat also points to CNA’s visible presence within the roofing industry and RIL itself. Through continued participation in board meetings, risk control workshops, association meetings and member events, the team has remained closely connected to the captive and responsive to its evolving needs. Rather than operating as a transactional vendor, CNA has worked alongside members and industry peers to strengthen the captive at every stage.
Sustaining the model
Building a successful captive is significant. Sustaining one for nearly two decades is far more difficult. Markets evolve. Captive leadership changes. Captive member companies grow, merge and transition to new generations of ownership. These natural evolutions create risk to the captive model and must be managed carefully to ensure success. RIL has endured many of these changes, yet it has remained grounded in the same principles that shaped it from the beginning, focusing on culture, improving risk management practices and making an impact on the broader commercial roofing industry.
To ensure RIL is around for generations to come, financial stability has always been a central focus area. Since its inception, the captive has paid $141 million in declared distributions and experienced a 98% historical retention rate. This strong financial foundation allows the captive to invest beyond its core operations, supporting member education, leadership development, industry advancement, innovative technology partnerships, strategic vendor relationships and initiatives that contribute to the future of the roofing profession.
Sustaining a strong captive also means sustaining a strong profession and nurturing the next generation of leaders who will carry the industry forward.
“The captive provides opportunities for younger professionals to become engaged early in their careers whether through committee participation, educational events or executive committee service,” Rozwat explains.
RIL has found engaging with up-and-coming talent has been a mutually beneficial relationship.
“The captive has seasoned industry veterans whose experience provides stability and historical context, and emerging leaders bring fresh ideas, new energy and a different perspective,” Rozwat adds.
Ultimately, the success of RIL cannot be measured solely by underwriting performance or financial returns. Its greatest achievement is creating an environment where experience is shared rather than protected and where every generation inherits not only a stronger business but also a stronger industry.
Houck captures that mindset best: “Every member is a contributor and a learner. You always walk away learning something.”
Nearly two decades after its inception, RIL stands as proof that joining a group captive is far more than signing on for an insurance program. Rather than simply being transactional, the captive is a community built on trust, a dedication to risk management and a genuine desire to learn alongside peers. With this philosophy in place, the value extends beyond member balance sheets to the larger roofing industry as a whole.
MARK WILKE
Vice president and head of specialized construction and commercial captives
CNA, Chicago
