Head of Compliance

Position Summary: The Head of Compliance is Florida Re’s senior compliance executive, accountable for designing, implementing, and leading the company’s enterprise-wide compliance program. This individual serves as the primary point of contact with the Florida Office of Insurance Regulation (Florida OIR) and other state and federal regulators, owns the company’s regulatory filings and licensing posture, and advises the CEO and Board on compliance risk across underwriting, claims, capital, sanctions, and data governance. The role carries direct authority to escalate concerns to the Board and stop-work authority on activity that presents material regulatory or reputational risk.

Key Responsibilities: Regulatory Strategy & Relationship Management Serve as Florida Re’s primary liaison to the Florida Office of Insurance Regulation (OIR), the Florida Department of Financial Services, and, where applicable, out-of-state and offshore regulators for affiliated or fronted business. Own all regulatory filings required under the Florida Insurance Code (Fla. Stat. ch. 624, 625, and 628), including financial statement filings, holding company filings (Form B/C), and reinsurance-related disclosures. Monitor and interpret changes in Florida insurance law and NAIC model laws as adopted in Florida, and translate them into practical changes to policy, systems, and controls. Lead or coordinate Florida Re’s participation in financial and market conduct examinations. Reinsurance & Capital Compliance Maintain Florida Re’s compliance with Florida’s credit-for-reinsurance framework (Fla. Admin. Code r. 69O-144), including collateral, trust, and certified/eligible/accredited reinsurer requirements for all retrocession and fronting counterparties. Oversee compliance elements of the company’s Own Risk and Solvency Assessment (ORSA) and Risk-Based Capital (RBC) reporting in line with NAIC guidance. Support the Corporate Governance Annual Disclosure and coordinate with Finance and Actuarial on statutory capital, surplus, and rating-agency (AM Best, Demotech, S&P) compliance requirements. Review reinsurance and retrocession agreements, side letters, and collateral arrangements for regulatory and contractual compliance prior to execution. Enterprise Compliance Program Build and maintain Florida Re’s compliance policies, procedures, and internal controls, including a documented compliance risk assessment refreshed at least annually. Design and deliver company-wide compliance training, including licensing, anti-fraud, anti-money laundering (AML)/OFAC sanctions screening, and data security awareness. Own the company’s producer and entity licensing compliance where Florida Re engages in activity requiring licensure. Administer the code of conduct, conflicts-of-interest disclosures, gifts and entertainment policy, and whistleblower/reporting channel, investigating matters raised and reporting outcomes to the Board. Maintain compliance with Florida’s Insurance Data Security Law (Fla. Stat. § 624.4211) and coordinate with IT/Security on data breach notification obligations. Governance & Reporting Prepare and present regular compliance reporting to the CEO, Executive Committee, and the Board Audit & Risk Committee, including emerging regulatory risk, open findings, and remediation status. Partner with Legal, Actuarial, Underwriting, Claims, and Finance to embed compliance requirements into day-to-day business processes rather than operating compliance as a standalone check. Track and manage regulatory examinations, inquiries, and correspondence to closure, maintaining an audit-ready record of the company’s regulatory posture. Recommend and, once approved, build out the compliance team’s structure and resourcing as Florida Re’s premium volume and geographic footprint grow.

Qualifications: Required Bachelor’s degree in business, finance, law, risk management, or a related field; JD, MBA, or advanced degree a plus.10+ years of progressive compliance, regulatory affairs, or legal experience within (re)insurance, with at least 5 years in a senior or leadership compliance role. Direct, hands-on experience with Florida insurance regulation and the Florida OIR, or comparable experience with another state insurance department and a demonstrated ability to get up to speed quickly on Florida’s regime. Working knowledge of NAIC financial regulation standards, including RBC, ORSA, Credit for Reinsurance, and Corporate Governance Annual Disclosure requirements. Property catastrophe or reinsurance market experience (broker, reinsurer, or carrier side) strongly preferred given Florida Re’s business model. Demonstrated experience managing regulatory examinations and building or scaling a compliance function. Preferred Professional certification such as CCEP, CPCU, ARe, CIC, or equivalent. Familiarity with Bermuda, Cayman, or other offshore reinsurance market regulation, given the sector’s reliance on non-U.S. retrocessional capacity. Prior experience reporting to a Board Audit & Risk Committee or serving as a company’s designated Chief Compliance Officer. Existing professional relationships within the Florida OIR, NAIC, or Florida property/reinsurance market (e.g., FAIR, RAA).Skills &

Competencies: Sound, independent regulatory judgment and the confidence to escalate issues to executive leadership and the Board. Ability to translate complex statutory and regulatory requirements into clear, actionable guidance for non-compliance colleagues. High personal integrity and discretion in handling sensitive regulatory and investigative matters. Strong written and verbal communication skills, including comfort presenting to regulators, rating agencies, and the Board. Organized and detail-oriented, with the ability to manage multiple filings, deadlines, and examinations concurrently. Collaborative style suited to a lean, growing organization where compliance works closely with underwriting, actuarial, and finance.

Working Conditions: This role is based at Florida Re’s Tampa, Florida office, with regular in-office presence expected given the need for close, day-to-day coordination with underwriting, actuarial, finance, and executive leadership. Some travel is required for regulatory meetings and industry events.