Insurance Business Review: Specials Magazine

Loss control and claims handling have evolved from secondary concerns to frontline defenses in today’s risk management playbook. With rising claims costs and heightened reputational risks, businesses can no longer afford a reactive, wait-and see approach. Roosevelt Road Specialty redefines risk management by embedding proactive mitigation strategies directly into its underwriting process. As a managing general agent (MGA), Roosevelt Road prioritizes hands-on, people-first risk management in every client interaction. Whether through pre-bind inspections, on-site visits, or safety training, the company combines advanced analytics and next-generation predictive modeling with a boots-on-the-ground methodology. An internal team of labor law attorneys and specialized claims adjusters supports this effort. They thoroughly investigate incidents, assess liability, and facilitate claim resolutions with legal and industry-specific expertise. Businesses leverage these insights to implement tangible changes, modify risky behaviors and adopt practical measures that significantly reduce the likelihood of future claims. A Proactive Approach to Risk Management Roosevelt Road Specialty’s proactive mindset became even more critical in the post-2008 landscape. As industry consolidation pushed competitors to outsource essential services like claims handling and loss control, Roosevelt Road strengthened its in-house expertise. By keeping these functions within its core operations, the company delivers a specialized approach that reduces claim severity and maximizes long-term value for carriers, brokers, and insured parties. “Claims handling and loss control are often overlooked,” Dan Hickey Jr., founder and CEO, said. “We treat them as central to the process, giving our clients confidence that they have the best tools, strategies, and outcomes working in their favor.” With deep expertise in four key industries—construction, sports and entertainment, residential real estate, and senior living—Roosevelt Road tailors policies to the unique risks of each sector. Whether crafting flexible excess and surplus solutions or operating within the strict confines of standard coverage, the company ensures long-term stability by integrating a comprehensive risk strategy with every policy. Roosevelt Road proves that the smartest way to manage risk is to prevent it in the first place. The Growth Blueprint Roosevelt Road prioritizes organic growth over aggressive acquisitions, focusing on product diversification and geographic expansion to strengthen its market position. For instance, in the habitational real estate sector, the company goes beyond core coverages by layering complementary solutions such as property insurance and cyber insurance. An employment practices liability insurance (EPLI) package is under development and will be offered soon. This holistic approach results in a more comprehensive risk management package, providing clients with robust and tailored protection. A Meaningful Risk Participant Roosevelt Road stands out in the market by taking on a meaningful share of every risk it underwrites, unlike many MGAs that function purely as intermediaries with profit-sharing arrangements. Through Roosevelt Road in the U.S. and Roosevelt Road Re, Ltd., a Class 3B reinsurance company based in Bermuda, the firm has built a solid framework supporting long-term financial stability and disciplined growth. With over $1.5 billion in primary insurance written and reinsurance ceded to its Bermuda affiliates, its commitment to risk-sharing is both strategic and substantial.