Senior Living Insurance

Dan Hickey Jr. has over 30 years of extensive experience across the property and casualty insurance industry. He is the founding partner and CEO of Roosevelt Road Capital Partners (RRCP), a global insurance organization that wholly owns Tradesman Program Managers USA MGA, K&B Specialty Insurance, Renaissance Specialty Insurance, and Roosevelt Road Re, a dedicated MGU and Class 3B Bermuda-reinsurance company. Under his leadership, RRCP has grown premiums in excess of $1.3 billion, establishing itself as an industry leader in delivering best-in-class claims and loss control services to the construction market, real estate, sports, leisure and entertainment, and senior and assisted living sectors — all with exceptional underwriting results. Mr. Hickey served as chairman and CEO of Majestic Holdings, LLC and led the company to a successful public offering in 2005. He succeeded in turning Majestic Insurance Company, a B++ company, into an A- “AM Best”-rated company and grew premiums from $50 million to more than $150 million and expanded the business into four states. In 2016, with a visionary approach, recognizing and seizing the opportunity created by the dislocation in the New York construction market, Mr. Hickey founded Tradesman Program Managers (TPM) – a managing general agent specializing in contractors’ commercial general liability. Staffed by experts who specialize in detecting and prosecuting fraud, TPM launched a deep investigation in 2021 into fraudulent claims in the greater New York construction market uncovering 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. The initiative led to widespread legal action against predatory practices, which attracted attention from insurers around the country and from national media outlets such as the New York Post, ABC News, and Inside Edition. Mr. Hickey’s strategic insight and leadership have positioned him as a trusted authority within the industry. With a comprehensive understanding of the insurance model from top to bottom, Mr. Hickey possesses a rare ability to integrate and align key business disciplines, building and executing effective corporate strategies with precision and foresight. Mr. Hickey’s influence extends beyond business; he has an exemplary philanthropic record. He is a proud youth football coach and, for more than four decades, has hosted the Eileen Hickey Holiday Dinner on Thanksgiving and Christmas serving more than 1,500 people each holiday. Mr. Hickey received his B.A. in Business Administration from Northeastern University where he graduated cum laude.  

Rick Ecklord is the Chief Financial Officer of Tradesman Program Managers , bringing over 25 years of financial and investment experience to the firm since joining in 2019. Prior to TPM, Mr. Ecklord was the President and Chief Operating Officer of Sandell Re, Ltd., a Class 3A Bermuda reinsurer, which he founded in 2014. During this time, he also established SOBC Sandell, a joint venture focused on mid-cap investments in the insurance run-off sector.Mr. Ecklord spent 18 years at Sandell Asset Management, a global event-driven hedge fund, where he served as Partner and Senior Managing Director. In that role, he led investments in the merger arbitrage space. Earlier in his career, he held equity derivatives positions at Goldman Sachs and SLK Capital Markets, and was a member of the American Stock Exchange.Mr. Ecklord earned a Bachelor of Science in Business Administration, with a concentration in Finance, from The Citadel, The Military College of South Carolina in 1995.

Tom Kelly is a seasoned attorney admitted to practice in New York State with over 35 years of legal experience. He is also admitted to the U.S. District Courts for the Southern and Northern Districts of New York, as well as the U.S. Court of Appeals for the Second Circuit.Tom brings a deep and diverse background to the company, with a primary focus on personal injury litigation, insurance coverage disputes, and regulatory compliance. He has a particular expertise in New York Labor Law claims and plays a key role in collaborating with third-party administrators and outside counsel to deliver a strong and strategic defense.Throughout his career, Tom has represented a wide range of clients, including major insurance carriers such as Main Street America, Liberty Mutual, and Lloyd’s of London. He also serves as defense counsel for multiple municipalities, including the City of Poughkeepsie Police Department, the Town of Poughkeepsie, and Dutchess County, handling personal injury and constitutional claims.Outside of his professional work, Tom is actively involved in the greater New York community, serving on several civic and nonprofit boards. He resides in the region with his wife and their three children.

Anthony Dietz serves as the Chief Underwriting Officer at Roosevelt Road Specialty, bringing more than 25 years of experience across underwriting, brokerage, and executive leadership in the insurance industry.Before joining Roosevelt Road Specialty, Anthony was Head of Insurance Brokerage at Procore Risk Advisors. He has held several senior leadership roles, including Senior Vice President at NFP (an Aon company), Vice President at Arch Insurance Group Inc., and Regional Manager at AIG.Anthony holds a bachelor’s degree in Finance and Business Law from Hofstra University and an MBA in Management from the Fordham Gabelli School of Business in New York City.

Sean McDonnell is the Chief Marketing Officer of Roosevelt Road Specialty and has over two decades of specialized experience in the insurance industry. Sean has built a reputation for delivering tailored insurance solutions that meet the unique needs of trades professionals.Throughout his career, Sean has worked closely with retail agents and brokers across the country, providing expertise in underwriting, program development, and risk management. His strategic approach and hands-on industry knowledge have helped position Roosevelt Road Specialty as a trusted partner across the insurance industry.Sean is passionate about building long-term relationships and driving innovation in program management. His commitment to service, transparency, and reliability continues to shape the success of Roosevelt Road Specialty and its valued clients.

Greg Jablonsky has served as Chief Information Officer of Roosevelt Road Specialty since 2021, overseeing IT strategy and operations across all subsidiaries, including Roosevelt Road Reinsurance. Known for his strong communication skills and active listening, Greg brings a collaborative approach that bridges technology with business objectives.He works closely with cross-functional teams and frequently partners with the CFO on actuarial analyses, contributing a fresh perspective that enhances organizational efficiency. One of the key challenges he navigates is aligning stakeholder expectations with the time-intensive demands of IT projects—an area where his clarity and foresight are essential.With more than eight years of experience as a CIO, Greg has held leadership roles at the New York Power Authority and IBM. He earned a Bachelor of Science in Information Systems from Pace University and continues to embrace a forward-thinking “What’s Next” mindset in his professional growth.

Bryan Baird is the President & CEO of K&B Specialty Insurance (KBSI), which administers the CareAgents program through Roosevelt Road Specialty. A Registered Professional Liability Underwriter (RPLU) and a seasoned insurance executive with more than 20 years of experience, Bryan has a strong track record in business ownership, entrepreneurship, and direct sales within the senior care and residential facilities market.Before founding KBSI, Bryan built and led K&B Underwriters, a Managing General Agency (MGA) platform, serving as its President & CEO. He also played a key role in transforming the insurance quoting and binding process through the launch of xagent.com, an innovative digital platform that streamlines access to thousands of business lines and multiple carriers nationwide. Its signature "Input once and submit everywhere™" model has empowered insurance agents across all 50 states to generate bindable quotes within minutes.Known for his energy and forward-thinking leadership, Bryan continues to drive KBSI’s success with a focus on modernizing risk management and loss prevention solutions tailored to the senior care industry. His passion for innovation extends beyond insurance, as he works to bring meaningful change to the way care facilities approach risk.

Rian Girard serves as the Chief Underwriting Officer at K&B Specialty Insurance (KBSI), where he plays a key role in driving the profitability and strategic growth of the CareAgents senior living portfolio.Rian brings a wealth of experience to his role, having previously served as Chief Underwriting Officer at the Insurtech firm xagent, as well as holding senior underwriting and leadership positions at leading insurers such as Admiral, Zurich, and AIG. Rian holds the Chartered Property Casualty Underwriter (CPCU) designation. His deep industry knowledge, combined with a passion for innovation, enables him to navigate the complexities of building a high-performing, forward-thinking organization within the Roosevelt Road Specialty platform.Known for his disciplined and strategic approach, Rian is focused on fostering sustainable growth through lean operations, all while maintaining a commitment to delivering exceptional customer service. His leadership is rooted in operational excellence and shaped by a strong understanding of both traditional and tech-enabled underwriting environments.Rian holds a Bachelor of Science from the University of Notre Dame, where he was a member of the university’s fencing team—an experience that reflects his emphasis on precision, strategy, and competitive excellence in both sports and business.

As Vice President of Broker Relations at Roosevelt Road Specialty, Sam Hickey plays a critical role in fostering and expanding strategic broker partnerships across all four verticals of the organization. Leveraging a deep understanding of the New York construction market and extensive experience in both retail and wholesale insurance sectors, Sam brings a unique blend of market insight and industry expertise to the role.Sam is dedicated to advancing Roosevelt Road’s value proposition on a national scale. Through a focused and strategic distribution model, he underscores the company’s commitment to exceptional claims handling and industry-leading loss control services—delivering tailored solutions and unmatched support to clients nationwide.Sam is a certified Construction Risk and Insurance Specialist (CRIS) and holds the Associate in Risk Management (ARM) designation.Outside the office, Sam enjoys traveling, golfing, and spending time with friends and family, maintaining a balanced lifestyle alongside his professional pursuits.

Carrie Ginchereau is the Controller at Roosevelt Road Specialty, bringing over a decade of accounting and advisory expertise to the firm. She joined the company in 2024 and plays a key role in overseeing financial operations, reporting, and strategic planning initiatives.Prior to joining Roosevelt Road, Carrie held several positions at Wouch, Maloney & Co., LLP, where she most recently served as Manager of Business Advisory Services. In that role, she provided strategic financial guidance to a diverse client base. Her earlier roles as Senior Accountant and Junior Accountant at the same firm enabled her to develop a strong foundation in accounting principles and practices across multiple industries.Carrie is a Certified Public Accountant (CPA) and holds a Bachelor of Business Administration in Accounting from Temple University’s Fox School of Business and Management. She also earned a Master’s degree in Accounting from DeVry University.

Mark McDonnell is a seasoned insurance professional with Roosevelt Road Specialty, where he plays an integral role in driving strategic growth and delivering tailored risk solutions across the organization’s specialized verticals. With extensive experience in the insurance industry, Mark brings deep expertise in underwriting, broker relations, and program development.Known for his collaborative approach and sharp market insight, Mark is committed to building long-term partnerships and delivering exceptional value to both brokers and clients. His leadership supports Roosevelt Road’s mission to provide innovative coverage solutions backed by responsive service and a strong commitment to loss control and claims excellence.

Roger Flores is the Senior Vice President of Business Auto Underwriting at Roosevelt Road Specialty, where he leads the company’s auto underwriting operations. With more than 20 years of experience in the insurance industry, Roger brings a strategic, results-oriented approach and a broad skill set to his role.Before joining Roosevelt Road Specialty in 2023, Roger served as Vice President of Underwriting and Operations at American Millennium Insurance Company. In that role, he managed all underwriting functions as well as key business operations, including Information Technology, Real Estate, and Reinsurance.Roger began his career in claims at Crum & Forster Insurance and spent a total of nine years in claims roles, giving him a well-rounded and insightful perspective on risk assessment. This foundational experience allows him to approach underwriting with a proactive mindset, anticipating challenges and delivering solutions tailored to each client's needs.With a strong command of complex risk exposures and specialized insurance products, Roger is instrumental in driving Roosevelt Road Specialty’s underwriting strategy and supporting broker relationships. He is known for his analytical rigor, client-centric focus, and ability to craft customized insurance programs that respond to a dynamic marketplace. Roger works closely with brokers and internal teams to deliver sound underwriting decisions, responsive service, and long-term value for clients.Roger earned his Bachelor of Science degree in business management from Fairleigh Dickinson University – Madison.  He also possesses a Senior Claim Law Associate designation from the American Educational Institute.

Joe Mercurio Jr. is Senior Vice President of Loss Control for Tradesman Program Managers.

Throughout his career, Joe has led safety initiatives on some of the most high-profile construction projects in the New York region, including:

• 10 Columbus Circle with Structure Tone (SSM)

• 66 Hudson Blvd with Roger & Sons/Turner Construction (SSM)

• Hudson Yards Tower E with AECOM Tishman (CSFSM)

• Hudson Yards Retail and Tower A with W&W Steel Erectors (Safety Manager)

• Montreign Resort Casino at Adelaar with Yonkers Contracting (Safety Representative)

• Regeneron Pharmaceuticals with Belway Electric (Safety Representative)

• Winthrop University Hospital with Lendlease (Safety Representative)

Joe holds a broad array of professional certifications that reflect his commitment to excellence and safety in the field. He is a Certified Safety Professional (CSP), Licensed NYC Site Safety Manager (SSM), and OSHA Authorized Construction Trainer. His credentials also include:

• Associate Safety Professional (ASP)

• Construction Health and Safety Technician (CHST)

• Construction Site Fire Safety Manager (CSFSM)

• ATSSA Certified Flagging Instructor & Traffic Control Supervisor

• National Safety Council Defensive Driving Instructor

• 62 Supervisor SST Card

• 32-Hour Signal Person/Rigging Supervisor Trainer

• 32-Hour Rigging Supervisor

With a proven track record across diverse and complex job sites, Joe brings unparalleled expertise, regulatory knowledge, and leadership to every project he supports.

Jeffrey Feldman serves as Senior Vice President of Claims at K&B Specialty Insurance (KBSI), where he oversees the full spectrum of the company’s claims operations. His responsibilities include third-party administrator management, defense panel oversight, exposure assessment, reserving, and acting as a key liaison between the claims and underwriting teams. He also provides strategic support to marketing initiatives.With over 35 years of diverse claims experience - including extensive work on high-exposure CAT claims - Jeff is known for his ability to quickly assess complex situations and develop effective strategies to mitigate risk. A strong advocate for early claims investigation, he is committed to educating insureds and brokers on best practices, particularly in an environment where rising claim values and insurance fraud are increasing challenges for the industry.Jeff is also a dedicated mentor to emerging professionals on the claims team and takes pride in helping shape the next generation of industry talent. Prior to joining KBSI, he spent 25 years at AIG, including 20 years in senior management roles across reinsurance, excess claims, healthcare claims, and primary construction claims.Jeff holds a degree in economics from Binghamton University. Outside the office, he enjoys his passion for motorsports - especially riding his three-wheel motorcycle.

Anthony Baird comes from K&B Specialty Insurance (KBSI), a division of Roosevelt Road Specialty where he served as Operations Manager. Anthony played a key role in launching the CareAgents program and led the day-to-day operations with a focus on business process improvement, innovation, and IT strategy. With a unique background that blends underwriting expertise and technical acumen, Anthony is well-positioned to address a broad range of organizational challenges. He works closely with underwriting, claims, and finance teams to enhance operational efficiency, and is committed to building technology-driven solutions that streamline processes and drive meaningful impact. Anthony is particularly focused on emerging industry trends such as automation and data analytics. Before joining Roosevelt Road Specialty, he led operations at an Insurtech startup and held key roles at K&B Underwriters. He holds a bachelor’s degree from the University of Dallas. Outside the office, Anthony enjoys spending time outdoors—hiking, snowboarding, and, most recently, cycling.

Al Gutierrez brings over 30 years of insurance industry experience to his role as Vice President of Broker Relations, leading Roosevelt Road Specialty’s expansion efforts across the West Coast. With a career spanning regional and national insurance agencies as well as major carriers, Al possesses deep expertise in commercial insurance and a proven ability to navigate complex market dynamics.Known for his strategic foresight and innovative approach, Al excels at building strong, mutually beneficial relationships with brokers and carriers. His collaborative style creates “win-win-win” outcomes that deliver value across the board. His background in underwriting, distribution, and product development further strengthens his ability to support and empower broker partners.Al plays a critical role in advancing Roosevelt Road Specialty’s West Coast growth strategy. His deep understanding of the regional market, strong negotiation skills, and commitment to excellence position him as a trusted resource for our distribution partners. He also leverages the strength of our limited distribution model and state-of-the-art underwriting platform to deliver competitive advantages to those he works with.

Chris Enderes is Senior Vice President of Property at Roosevelt Road Specialty, where he plays an integral role in advancing the company’s specialized insurance offerings and operational excellence. With deep expertise in underwriting, broker relations, and operations, Chris brings both strategic insight and hands-on industry knowledge to his role.Known for his collaborative leadership style and results-driven approach, Chris works closely with internal teams and external partners to deliver innovative insurance solutions tailored to evolving market needs. He is a strong advocate for building long-term relationships with brokers, clients, and carrier partners, ensuring a high level of service and responsiveness.Prior to joining Roosevelt Road Specialty, Chris held key positions across the insurance sector, including Middle Market Property Executive Underwriter and Senior Package Underwriter.Chris’s broad perspective and commitment to excellence contribute to Roosevelt Road Specialty’s continued growth and reputation for quality.

Kristin Thorne is the Senior Vice President of Corporate Communications at Roosevelt Road Specialty. With over 20 years of experience in the media industry as an on-air investigative journalist, she most recently worked at WABC Channel 7 Eyewitness News.Kristin's reporting has earned her five Emmy Awards and two regional Edward R. Murrow Awards. She holds a master's degree in broadcast journalism from Northwestern University and a bachelor's degree from Georgetown University.

Jocelyn brings a comprehensive understanding of insurance coverage law, regulatory compliance, and New York State Labor Law litigation. Her unique experience representing both plaintiffs and defendants gives her a well-rounded perspective in managing coverage issues and legal risk. She remains committed to ongoing professional development and stays at the forefront of evolving legal trends, case law, and industry regulations.Admitted to practice law in the State of New York and the Southern District of New York federal court, Jocelyn has developed a reputation for her thorough legal analysis and strategic approach to complex insurance matters. In addition to her role at Tradesman, she serves as General Counsel for Roosevelt Road Re, contributing her legal insight to broader organizational initiatives.Jocelyn earned her Juris Doctor from New York Law School and is an active member of the New York City Bar Association, where she contributes to both the Insurance Law and Animal Law Committees.

Jim Kilduff is the Director of Reinsurance and Business Development at Roosevelt Road Specialty where he brings more than four decades of experience in the insurance industry with a strong focus on program development, underwriting strategy, and carrier relations. Known for his deep market knowledge and collaborative approach, Jim plays a critical role in driving growth and success of Roosevelt Road Specialty's insurance offerings.Throughout his career, Jim has built a reputation for developing innovative, client-focused solutions tailored to niche industries and emerging risks. His ability to align underwriting performance with strategic goals has earned him the trust of brokers, MGAs, and carrier partners alike. At Roosevelt Road Specialty, Jim is instrumental in structuring and managing programs that deliver both profitability and long-term value to insureds.Jim's leadership is grounded in integrity, responsiveness, and a genuine commitment to build strong, sustainable partnerships across all areas of the insurance value chain. His experience spans both the retail and program sides of the business, giving him a comprehensive perspective that informs every aspect of his work.As Roosevelt Road Specialty continues to grow, Jim remains focused on delivering underwriting excellence, operational efficiency, and outstanding service to clients around the globe.

Toni Malicdem serves as Senior Clinical Risk Manager at K&B Specialty Insurance, where she brings extensive experience in healthcare-related insurance and a passion for supporting those who provide care in our communities. In her leadership role, Toni oversees strategic development, risk management and loss control, as well as broker relationships within the CareAgents division, which focuses on delivering specialized insurance solutions for senior living providers.With a strong background in program management and a deep understanding of the unique risks facing the care industry, Toni is known for her ability to craft tailored insurance programs that align with both regulatory requirements and real-world operational needs. Her collaborative style and client-first mindset have helped establish K&B Specialty Insurance as a trusted partner for agents and insureds nationwide.Toni is committed to advancing the mission of CareAgents by combining thoughtful risk management strategies with responsive, hands-on service. Her leadership continues to drive innovation, strengthen relationships, and support the growth of the care industry through reliable, forward-thinking insurance solutions.