Associate Director, Tax

Oscar Health
Boston, MA

Hi, we're Oscar. We're hiring an Associate Director, Tax to join our Finance. Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family. About the role: The Associate Director, Tax leads income tax compliance including tax provisions under Generally Accepted Accounting principles (GAAP) and Statutory reporting, federal, state and local tax returns, and tax planning and projects. The Associate Director, Tax supports the Tax leadership team in developing department strategy. You will report into the Sr. Director, Tax. Work Location: This is a remote position, open to candidates who reside in: Boston, MA. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area. #LI-Remote Pay Transparency: The base pay for this role is: $162,453 - $213,220 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses. Responsibilities: Manage the annual and quarterly tax GAAP and Statutory tax provision processes and lead the related internal and external relationships necessary to support these processes. Review U.S. federal, state, and local tax returns and estimates for the corporate holding companies and insurance subsidiaries and manage our relationship with external consultants on this work. Ensure integrity of tax accounting and compliance results using technology solutions, partnering with the Finance Transformation Team and the Company's external vendors. Manage tax responses to audits and notices and the related correspondence with internal and external parties. Ensure compliance with indirect tax compliance functions. Lead the preparation of financial data and analysis to support tax forecasting and projects. Partner with areas of Finance and the business to address tax issues and meet organizational goals. Stay abreast and educate others on developments within the insurance tax area and their possible effects to the Company. Help develop and implement tax strategies and planning opportunities. Automate processes to refine tax compliance and provide analytical insights. Compliance with all applicable laws and regulations. Other duties as assigned. Requirements: Bachelor's degree in Accounting, or 4 years commensurate experience. 7+ years of tax experience in a public accounting firm or equivalent experience in a corporate tax department. Proficient in using code and regulations. Strong knowledge in ASC 740. 3+ years experience as a team leader. Bonus points: CPA and/or Master's of Taxation. Statement of Statutory Accounting Principle (SSAP) 101 reporting. Knowledge of domestic tax issues affecting U.S. insurance companies. Experience implementing tax provision software. Work with large datasets to build models and leverage tools. Experience with state tax nexus considerations. This is an authentic Oscar Health job opportunity. Learn more about how you can safeguard yourself from recruitment fraud here. At Oscar, being an

Posted 2026-07-05

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