Sports, Leisure & Entertainment 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, K&B Specialty Insurance, Renaissance Specialty Insurance, RISE Habitational, 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 Roosevelt Road Specialty, bringing over 25 years of financial and investment experience to the firm since joining in 2019. Prior to Roosevelt Road Specialty, 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 is a seasoned insurance executive with over 25 years of experience in underwriting, brokerage, and executive leadership. He currently serves as the Chief Underwriting Officer at Roosevelt Road Specialty, where he oversees all Managing General Underwriter (MGU) units nationwide. In this role, he focuses on developing specialized coverages for construction projects and wrap-up programs.

Prior to joining Roosevelt Road Specialty in August 2024, Anthony was the Head of Insurance Brokerage at Procore Risk Advisors. There, he led initiatives to modernize the insurance buying process for construction clients, advocating for data-driven risk management and more nuanced underwriting approaches.

Anthony's earlier career included senior leadership positions such as Senior Vice President at NFP (an Aon company), Vice President at Arch Insurance Group Inc., and Regional Manager at AIG. His expertise encompasses brokerage, underwriting, and team leadership across various sectors of the insurance industry.

He holds a Bachelor of Business Administration in Finance and Business Law from Hofstra University and an MBA in Management from the Fordham Gabelli School of Business.

Anthony continues to influence the insurance industry through his leadership and innovative approaches to risk management

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.

Greg Mosher is a distinguished business and insurance executive, entrepreneur, and visionary leader with an impressive track record spanning over 40 years. Throughout his career, he has demonstrated a relentless commitment to transforming businesses and markets through a growth and value-oriented mindset.As the CEO of Renaissance Specialty Insurance Group, a managing general agency he founded in 2020, Mr. Mosher has taken the company to new heights in a short span. Specializing in insuring collegiate, amateur, and professional sports, leisure, and entertainment risks, the company achieved a remarkable $35 million in premium production within its first 12 months.Prior to founding Renaissance, Mr. Mosher served as the CEO of Specialty Insurance Group, which grew at annual rates of 35% to 45%. Under his leadership, the company generated over $215 million in profitable premium within five years of its launch.One of Mr. Mosher's most notable achievements was as the CEO of K&K Insurance Group, where he played a pivotal role in establishing the company as the world leader in sports, leisure, and entertainment insurance. Following an acquisition by Lincoln National Corporation, he also served as the CEO of Lincoln National Specialty Reinsurance Company, managing $700 million in premium for the K&K/Lincoln companies.In addition to his insurance ventures, Mr. Mosher served as the Chairman and CEO of Workflow Management, overseeing its growth from $400 million to over $1 billion in revenue in just five years. He navigated the company through major financial transactions, including privatization, mergers, acquisitions, and divestitures totaling several hundred million dollars.Mr. Mosher's diverse expertise extends to various industries, including technology, real estate, aviation, and beyond. As the founder of ITC Media Conferencing, he pioneered the world's first extensive audio and video conferencing platform for international business-to-business communications, achieving revenue growth from startup to over $250 million.Throughout his career, Mr. Mosher has exhibited a unique blend of strategic acumen, financial expertise, and a relentless drive for success, solidifying his reputation as a transformative leader in the business and insurance sectors.

Chris Smyth serves as the Chief Underwriting Officer at Renaissance Specialty Insurance, bringing more than two decades of experience in program development and underwriting, specializing in niche markets. He is known for his strong leadership, strategic client relationships, and disciplined focus on underwriting profitability.Throughout his 19-year career, Chris has held a range of leadership roles, most recently as Program Director for NSM Insurance’s Sports and Wellness program. His expertise lies in aligning insurance products with the evolving needs of the sports, leisure and entertainment sectors, ensuring clients are protected as they expand and adapt to market changes.At Renaissance Specialty Insurance, Chris is dedicated to driving sustainable growth and delivering long-term value through innovative program development and operational excellence.Chris holds a Bachelor of Science in Finance from Saint Joseph’s University in Philadelphia, where he graduated cum laude, and is a licensed property and casualty agent. 

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 construction business 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 Specialty'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 Commercial 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 at Tradesman Program Managers and has been instrumental in promoting safety across some of the most complex and high-profile construction projects in the New York metropolitan area. His project portfolio includes serving as Site Safety Manager for Structure Tone at 10 Columbus Circle and for Roger & Sons/Turner Construction at 66 Hudson Boulevard. He also served as Construction Site Fire Safety Manager for AECOM Tishman at Hudson Yards Tower E. Additional roles include Safety Manager for W&W Steel Erectors at Hudson Yards Retail and Tower A, and Safety Representative for Yonkers Contracting at the Montreign Resort Casino, Belway Electric at Regeneron Pharmaceuticals, and Lendlease at Winthrop University Hospital.

Joe holds numerous industry certifications and is committed to upholding the highest standards in construction safety. He is a Certified Safety Professional (CSP), Associate Safety Professional (ASP), and Licensed NYC Site Safety Manager (SSM). His qualifications also include Construction Health and Safety Technician (CHST), Construction Site Fire Safety Manager (CSFSM), and OSHA Authorized Construction Trainer. He holds a 62-Hour Supervisor SST Card, and is certified as a National Safety Council Defensive Driving Instructor, ATSSA Flagging Instructor, and Traffic Control Supervisor. He is also qualified as a 32-Hour Signal Person/Rigging Supervisor Trainer and a 32-Hour Rigging Supervisor.

Joe’s depth of knowledge, extensive field experience, and dedication to safety make him a trusted leader in construction risk management and site safety operations.

Anthony Baird joined Roosevelt Road Specialty 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.Anthony holds a bachelor’s degree from the University of Dallas.Outside the office, he 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.

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 in New York.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 in American studies.

Joe Boyd serves as Vice President of Underwriting at Renaissance Specialty Insurance. With more than 20 years of experience in the commercial property and casualty insurance industry, Joe brings a well-rounded background that includes underwriting, claims, loss prevention, product management, compliance, and agency relations.Over the past 15 years, Joe has worked with managing general agencies (MGAs), focusing on both admitted and non-admitted lines. For the last five years, he has specialized in underwriting for the amusement and entertainment industries, developing tailored solutions for these complex, high-exposure sectors.Joe holds a bachelor’s in economics and a Master of Business Administration in finance from the University of Illinois. He also carries several professional designations, including Chartered Property Casualty Underwriter (CPCU), Associate in Risk Management (ARM), Associate In Claims (AIC), and Associate in Reinsurance (ARe), reflecting his deep commitment to industry expertise and professional excellence.

Jennifer Pymm, Esq., is a highly accomplished legal professional with extensive experience in insurance litigation, claims management, and legal strategy. She currently serves as Associate General Counsel at Tradesman Program Managers, where she leads the company’s claims operations with a focus on achieving strategic, results-driven outcomes.In her role, Jennifer oversees a diverse team of attorneys and senior claims executives, guiding the management of all claims and litigation activities, including those handled by Gallagher Bassett, Tradesman’s third-party administrator (TPA). She works closely with defense counsel and leverages her combined legal and claims expertise to ensure efficient and effective resolution of matters. Jennifer also maintains strong relationships with brokers, providing regular claim updates and facilitating collaborative claim reviews.Prior to joining Tradesman, Jennifer had more than 13 years of experience in private practice in New York, as well as tenure with two major insurance carriers. She held strategic leadership roles, including Senior Vice President of Claims and Senior Litigation Manager. Her background included supervising claims at the TPA level, giving her a comprehensive understanding of the full claims lifecycle from multiple industry perspectivesJennifer is deeply committed to fostering a collaborative, high-performing environment at Tradesman, and has been a key part of the company’s significant growth over the past three years.She is admitted to practice law in New York and is also admitted to the Southern, Eastern, and Northern Districts of New York, the Second Circuit Court of Appeals, and the United States Supreme Court - reflecting her broad legal authority and expertise.

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.

Lily Hickey serves as the Director of Claims for Roosevelt Road Specialty’s RISE and Renaissance programs, where she leads the claims operations with a focus on delivering timely, fair, and policy-compliant outcomes. A licensed independent adjuster with the Associate in Risk Management (ARM) designation, Lily brings a strong technical background and a collaborative, client-centered approach to her work.With a deep understanding of both the habitational and sports & leisure insurance sectors, Lily provides strategic oversight and hands-on leadership across the companies' claims portfolios. She manages a dedicated team, working closely with adjusters, legal partners, and internal departments to ensure efficient resolution, policy adherence, and clear communication with all stakeholders. Her leadership prioritizes transparency, responsiveness, and alignment between claims handling and overall client satisfaction.Lily is known for navigating complex claims with precision and professionalism, always keeping the insured’s experience at the forefront. Her guidance continues to reinforce RISE and Renaissance’s shared reputation for reliability, integrity, and excellence in claims service.