New York, NY – Jan. 23, 2026 – Roosevelt Road Specialty, a leading specialty insurance platform serving construction, habitational real estate, sports, entertainment, and other complex risk sectors, today announced the appointment of James Wrynn as the Global Chief Compliance Officer, further reinforcing the firm’s commitment to best-in-class governance and regulatory leadership.
In this enterprise-wide role, Mr. Wrynn will oversee global compliance strategy, regulatory engagement, internal controls, and governance frameworks across Roosevelt Road Specialty’s expanding portfolio of specialty programs and managing general agency operations.
“Compliance is a core pillar of our operating model,” said Daniel Hickey Jr., Chief Executive Officer of Roosevelt Road Specialty. “As we scale across jurisdictions and increasingly complex lines of business, strong, centralized compliance leadership is essential. This appointment reflects our commitment to building a durable, well-governed platform.”
Mr. Wrynn is one of the leading experts on insurance matters based on his more than 40 years of professional experience as an attorney, regulator, executive, director, and advisor. He has been involved in domestic and global insurance regulation and in assisting clients in developing strategies and programs dealing with regulatory issues, claims administration and analysis, identification of strategic partners, mergers/acquisitions and portfolio transfers.
Most recently, Mr. Wrynn served as Senior Managing Director at FTI Consulting. His previous positions include Chief Commercial Officer and Hearing Officer at National Arbitration and Mediation, Managing Director and Vice Chair for Guy Carpenter’s Global Strategic Advisory Group in the U.S., and Senior Partner at the Law Offices of Goldberg Segalla, LLP.
Before joining Goldberg Segalla, Mr. Wrynn served as the 40th and final Superintendent of the New York State Insurance Department. He was involved in the drafting of the new financial services law in New York and the merger of the Insurance Department with the NYS Department of Banking to form the new Department of Financial Services. During that time, he served as the first Executive Deputy Superintendent of DFS which oversaw the regulation of more than 1,700 insurance companies. He also previously served as the Executive Director of the New York State Insurance Fund, which is the largest provider of workers’ compensation insurance in New York state.
Mr. Wrynn is admitted to practice law in the federal and state courts of New York and New Jersey, and the U.S. Supreme Court. He holds an Associate in Captive Insurance (ACI), an Associate in Claims (AIC), an Associate in Risk Management (ARM), and a Workers’ Compensation Professional (WCP) designation and has served as a registered foreign lawyer in the United Kingdom and as a director on boards in the US, EU, and Bermuda.
