Associate Director, Corporate Compliance

Hi, we’re Oscar. We’re hiring an Associate Director, Corporate Compliance to join our Corporate Compliance team.

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.

The Associate Director, Corporate Compliance is responsible for training, investigating, monitoring, and enforcing programs, policies, and practices to ensure all applicable operational functions are in compliance with federal, state and local regulatory requirements. The Associate Director manages compliance efforts for Oscar’s licensed entities delivering Qualified Health Plans (QHPs) in the individual and small group markets, and works with leadership and the larger Compliance team to advise on serving third‑party QHP clients.

He/she will build a robust and best‑in‑class compliance program, including the seven elements of an effective compliance program as published by the Office of the Inspector General. The Associate Director partners with operational leaders to identify compliance risk, implement corrective action plans, and promote a culture of integrity and excellence across the organization.

Reporting to the Director, Corporate and Regulatory Compliance, the Associate Director will operate from the New York City office, with a hybrid work schedule of three days in‑office per week. Thursdays are a required in‑office day for team meetings and events; the other two days are flexible.

Base pay: $149,040 – $195,615 per year.

Eligible benefits include an unlimited vacation program, annual performance bonuses, medical, dental, and vision benefits, 11 paid holidays, paid sick time, paid parental leave, 401(k) plan participation, life and disability insurance, and paid wellness time and reimbursements.

• Lead, mentor, and support the Compliance team across all lines of business, encouraging professional development and advancing institutional compliance knowledge.
• Support the design, implementation, and continuous improvement of the corporate compliance program to promote an organizational culture of responsibility and accountability.
• Monitor and interpret federal and state regulations to guide business strategies that exceed industry standards for insurers, tech innovators, and public companies.
• Lead compliance investigations, assess adherence to obligations, and oversee development and monitoring of effective corrective action plans.
• Develop and manage comprehensive compliance training programs organization‑wide.
• Produce and deliver clear, actionable compliance reports tailored for all organizational levels, including executive leadership and external regulatory bodies.
• Partner with Risk and Controls to manage regulatory risk sustainably while deploying scalable compliance functions that support Oscar’s technology, strategic partners, and business growth.
• Lead the Compliance team in regulatory implementations and monitoring.
• Serve as a TEFCA subject matter expert.
• Ensure compliance with all applicable laws and regulations.
• Perform other duties as assigned.

• 7+ years of experience in a healthcare compliance setting, specifically in healthcare compliance, regulatory affairs, or related experience.
• 5+ years of experience managing effective compliance teams.
• 5+ years of experience applying state and federal health insurance statutes, regulations, marketplace, and MA requirements to meet reporting and audit obligations.

• Operational or internal audit experience.
• Enterprise risk management experience.
• HIPAA security experience.
• Experience in a start‑up and/or health tech environment.

At Oscar, being an Equal Opportunity Employer means more than upholding discrimination‑free hiring practices. We cultivate an environment where people can be their most authentic selves and find belonging and support. We are committed to anti–discrimination and equal access for all employees, contractors, and customers.

Oscar applicants are considered solely on qualifications, without regard to disability or accommodation needs. Applicants requiring accommodations during the application process should contact the Oscar Benefits Team at

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