A highly rated, nationally recognized insurance organization is seeking a Director of Tax Strategy to join their growing finance and tax leadership team. This is a confidential search for a senior professional who can bring deep expertise in insurance company taxation, reinsurance structuring, and international tax strategy — including emerging frameworks such as OECD Pillar Two and Bermuda tax regulation. As the Director of Tax Strategy, you’ll serve as a key advisor and thought leader, influencing the organization’s most important strategic initiatives. You’ll evaluate and optimize tax implications for domestic and international transactions, collaborate with senior executives across business lines, and help position the company for continued profitable growth.

Advise on tax implications of major business initiatives, including reinsurance, M&A, and entity structuring. Review transaction documents and treaties, leveraging internal experts and external advisors. Prepare tax accounting policy memos and documentation supporting key positions. Collaborate with finance and planning teams on GAAP, statutory, and Bermuda regulatory modeling. Monitor and interpret tax legislative changes, communicating strategic impacts to leadership. Identify and develop proactive tax planning strategies to enhance enterprise value.

10–15 years of progressive tax experience, including at least 10 years in the insurance or reinsurance. Deep expertise in U.S. insurance taxation, statutory accounting, and reinsurance transactions. Strong understanding of international tax frameworks (Bermuda and OECD Pillar Two preferred). Proven ability to synthesize complex financial data into clear, actionable insights. Excellent communication and collaboration skills with executive stakeholders. Bachelor’s degree required; CPA, MBA, or FSA highly preferred. Experience with sidecars and Bermuda structures a strong plus.