Roosevelt Road Specialty
Strengthening Risk Management Through Proactive Strategies

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.

This philosophy is reinforced by a carefully structured distribution model. Instead of pursuing high-volume growth, Roosevelt Road partners exclusively with select wholesale brokers to ensure its solutions reach specialized markets. By collaborating with brokers, real estate developers, contractors, and assisted living operators, it creates customized coverage solutions that address real-world challenges. This consultative, open-door model remains a defining feature of its operations.

Turning Uncertainties into Opportunities

In sports, entertainment, and live events, every moment presents both opportunity and risk. Whether ensuring a sold-out stadium concert, a high-stakes championship game, or a massive music festival, Roosevelt Road Specialty delivers specialized claims management and customized coverage strategies, allowing organizers to focus on unforgettable experiences while safeguarding their investments.

With primary coverage of up to $2 million per occurrence and $4 million aggregate—plus an additional $3 million in excess coverage—Roosevelt Road builds adaptive policies designed for today’s evolving risks. Through loss control evaluations, risk management policy reviews, claims coordination, and ongoing assessments, Roosevelt Road assists clients in staying ahead of emerging threats and reinforcing financial resilience. In an industry where every second counts, Roosevelt Road ensures that risk never steals the spotlight.

Fraud Prevention: A Mission, Not a Cost

Insurance fraud, particularly in high-risk industries like construction, can drive up costs and destabilize markets. Roosevelt Road has made fraud prevention a core mission, safeguarding clients while elevating integrity across the industry.

A deep investigation into fraudulent claims in the Greater New York construction market uncovered a troubling pattern: staged accidents, undocumented workers filing multiple claims and suspiciously identical injury reports, all linked to coordinated efforts by plaintiff attorneys and medical providers.

Where others might accept fraud as a cost of doing business, Roosevelt Road took action. By deploying aggressive loss control measures and proactive notification systems, it exposed deceptive activities that others overlooked. As a result, hundreds of fraudulent claims—many valued in the millions—were withdrawn before reaching trial.

This initiative also led to widespread legal action against predatory practices, which attracted national media attention from outlets such as the New York Post, ABC News, and Inside Edition.

Roosevelt Road’s dedicated anti-fraud unit is at the core of its success. Staffed by experts who specialize in detecting and prosecuting fraud, Roosevelt Road emphasizes direct engagement and real-world intelligence to catch fraud where it happens.

Unlike many insurers that rely heavily on automation, Roosevelt Road emphasizes direct engagement and real-world intelligence to catch fraud where it happens.

One of its most impactful tools is the Employer Notification Service (ENS), which conducts over 1,800 in-person site visits annually across a network of 300 contractor clients. These targeted assessments uncover red flags, prevent false claims, and provide businesses with real-time risk prevention strategies.

“Fighting fraud is expensive and time intensive. But for us, it’s not about the cost—it’s about the value,” Hickey Jr. said. “Every dollar we invest in protecting our clients and partners helps them thrive in this business.”

Technology for a Smarter Future

Roosevelt Road’s fraud prevention efforts are strengthened by cutting-edge technology woven into every aspect of its operations. From underwriting and claims processing to risk mitigation, its tech-driven approach enhances accuracy and efficiency.

For example, every vehicle in its program is equipped with dual-facing cameras, ensuring accountability and safety. In construction, the firm has pioneered I-Guard safety goggles equipped with built-in cameras that capture 90 minutes of real-time job site footage. This technology provides irrefutable evidence in liability disputes, disproving false injury claims and verifying compliance with safety protocols.

Beyond hardware, Roosevelt Road integrates proprietary safety applications and software that seamlessly connect with client operations. These tools enable real-time reporting, precise tracking, and early fraud detection, allowing businesses to act swiftly against fraudulent claims.

“Speed, accuracy and substance - these are our guiding principles,” Hickey Jr. explained. “We leverage technology without bureaucratic slowdowns, giving us a competitive edge in identifying risks and mitigating losses.”

Roosevelt Road also equips clients with AI-driven catastrophe (CAT) modeling to anticipate and prepare for natural disasters. Whether facing hurricanes, wildfires, or severe storms, its insurtech platform delivers real-time insights, exposure mapping, and proactive mitigation strategies, helping businesses manage large-scale risks with confidence.

Roosevelt Road Specialty: Redefining Risk Through Proactive Innovation

Roosevelt Road is redefining risk management by prioritizing proactive loss control, hands-on claims handling and fraud prevention, ensuring long-term stability for its clients. Through product diversification, strategic risk-sharing and cutting-edge technology, the company continues to innovate while expanding its market presence. By integrating real-time analytics, AI-driven catastrophe modeling and specialized safety solutions, Roosevelt Road empowers businesses to stay ahead of emerging threats. As industries evolve, Roosevelt Road remains committed to transforming uncertainties into opportunities, reinforcing resilience, and setting new standards in risk management.

Navigating New Horizons

From pioneering patient safety solutions in assisted living to deploying non-invasive technology platforms that enhance client privacy, Roosevelt Road has been anticipating and neutralizing adversities in the multiple industries in which it operates.

Now, it has set its sights on the burgeoning energy sector. This expansion presents an exciting opportunity to apply its loss control strategies to tackle the new challenges in complex energy infrastructures. With renewable energy projects on the rise, Roosevelt Road is developing expert solutions to address the unheard risks associated with wind and solar farms, ensuring its clients stay ahead of the evolving market curve.

With uncertainty looming over the insurance industry, Roosevelt Road offers more than just a blueprint for resilience. It instills confidence in the face of risk. After all, risk in insurance isn’t just managed; it’s mastered. And at Roosevelt Road, it’s sculpted with precision, orchestrated with foresight and wielded with a competitive edge to make every policy stand as a fortress against the unpredictable.