Senior Director, Enterprise Compliance

name; New York (NY); Hybrid; USD 219,000 - 287,000; Full time

Benefits offered by this job

Unlimited vacation

Equity grants

Annual performance bonuses

Job summary

Oscar Health in New York City is seeking a Senior Director, Enterprise Compliance to lead and evolve our enterprise compliance program within a fast‑growing, technology‑driven health insurer.

You will partner with Legal, Privacy, Security, Internal Audit and others to embed strong regulatory controls, guide executives, oversee investigations and education, and ensure alignment with federal and state healthcare requirements.

Qualifications

• 12+ years of progressively responsible experience in healthcare compliance, regulatory affairs, or enterprise risk management.
• 5+ years leading high‑performing compliance teams and enterprise‑wide initiatives.
• Experience designing and maintaining a healthcare compliance program aligned with OIG guidance and regulations.
• Experience with regulated healthcare organizations (health plans, managed care, or health‑tech).
• Track record translating regulatory developments into enterprise priorities and controls.
• Strong written and verbal communication skills with executive audiences.

Responsibilities

• Lead the execution and continuous improvement of Oscar’s enterprise compliance program, including strategy, work plans, risk assessments, policy governance, and monitoring.
• Translate priorities into operating plans; establish governance, allocate resources, and develop managers/teams.
• Advise senior leaders on regulatory impacts for products, markets, and operating models across lines of business.
• Oversee investigations, hotline, Special Investigations Unit, remediation, and escalation of significant concerns.
• Partner with Legal, Privacy, Security, Internal Audit, Enterprise Risk, Clinical, Product, Operations, and People teams to embed compliance into business processes.
• Set enterprise standards for ethics and compliance through education, communications, and awareness initiatives.
• Lead reporting for executive leadership, Compliance Committee, Board committees, and regulatory examinations; liaise with regulators/auditors.

Skills

Regulatory compliance

Leadership

Strategic planning

Communication

Risk management

Job description

Hi, we’re Oscar. We’re hiring a Senior Director, Enterprise Compliance to join our 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.

About the role:

The Senior Director, Enterprise Compliance supports the execution and continuous improvement of Oscar’s enterprise compliance program. Reporting to the Chief Compliance Officer, you will provide leadership over key compliance functions, including regulatory compliance, regulatory change management/implementation, compliance operations, investigations, monitoring and auditing, policy governance, and compliance education. You will anticipate regulatory and industry developments, translates them into enterprise compliance priorities, and partners with cross‑functional leaders to identify and mitigate compliance risks, strengthen internal controls, and promote a culture of ethics and integrity. You will exercise significant independent judgment, develops a compliance organization, and serves as a trusted advisor to business leaders on complex healthcare regulatory matters.

You will report into the Vice President, Chief Compliance Officer.

Work Location:

This position is based in our New York City office, requiring a hybrid work schedule with 3 days of in‑office work per week. Thursdays are a required in‑office day for team meetings and events, while your other two office days are flexible to suit your schedule. #LI-Hybrid

Pay Transparency:

The base pay for this role is: $218,592 - $286,902 per year. You are also eligible for employee benefits, participation in Oscar’s unlimited vacation program, company equity grants and annual performance bonuses.

Responsibilities:

• Lead the execution and continuous improvement of Oscar’s enterprise compliance program, including the multi-year compliance strategy, annual compliance work plans, risk assessments, policy governance, regulatory change management/implementation, monitoring, auditing, and reporting activities.
• Translate enterprise compliance priorities into an relevant operating plan; establish ownership and governance; allocate resources; develop compliance managers and team members; remove barriers; and lead accountability for measurable outcomes.
• Anticipate regulatory and industry developments and advise senior leaders on their possible effects for Oscar’s products, market participation, business strategy, and operating model. Provide guidance on federal and state healthcare regulations, contractual obligations, and emerging regulatory risks across applicable lines of business.
• Oversee compliance investigations, hotline reporting, the Special Investigations Unit, fraud‑prevention activities, corrective action plans, and remediation efforts, ensuring timely resolution and appropriate escalation of significant compliance concerns.
• Partner with leaders across Legal, Privacy, Security, Internal Audit, Enterprise Risk, Clinical, Product, Operations, and People teams to embed compliance requirements into business processes and strategic initiatives.
• Set and uphold enterprise standards for ethics and compliance by leading education, communications, and awareness initiatives that strengthen Oscar’s culture of ethics and compliance.
• Lead compliance reporting and engagement for executive leadership, Compliance Committee, Board committees, and regulatory examinations; support interactions with regulators and external auditors.
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• 12+ years of progressively responsible experience in healthcare compliance, regulatory affairs, legal compliance, audit, or enterprise risk management.
• 5+ years leading high‑performing compliance teams and enterprise‑wide compliance initiatives.
• Demonstrated experience designing, implementing, and maintaining an effective healthcare compliance program aligned with OIG Compliance Program Guidance and applicable federal and state regulations.
• Experience supporting highly regulated healthcare organizations, including health plans, managed care organizations, healthcare technology companies, provider organizations, or related entities.
• Track record of anticipating regulatory developments and translating them into enterprise priorities, operating plans, and business controls.
• Demonstrated experience leading complex compliance investigations, monitoring and auditing activities, regulatory risk assessments, corrective action planning, and policy governance.
• Experience advising senior business leaders on complex regulatory and operational compliance issues and leading their resolution
• Strong written and verbal communication skills, experience presenting to executive leadership, governance committees, regulators, or external auditors.

Bonus points:

• Experience supporting Marketplace and other applicable government or commercial health‑plan products.
• Experience leading compliance in a technology‑enabled, rapidly scaling, or operationally complex healthcare organization.
• Experience using data, technology, and automation to improve compliance monitoring, reporting, and program effectiveness.
• Healthcare compliance certification such as CHC, CHPC, CCEP, or comparable certification.
• JD, master’s degree, or other relevant advanced education.

This is an authentic Oscar Health job opportunity.

Artificial Intelligence (AI):

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Reasonable Accommodation:

Oscar applicants are considered solely based on their qualifications, without regard to applicant’s disability or need for accommodation. Any Oscar applicant who requires reasonable accommodations during the application process should contact the Oscar Benefits Team ([e-mail]) to make the need for an accommodation known.

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Pay Transparency:

Final offer amounts, within the base pay set forth above, are determined by factors including your relevant skills, education, and experience. Full‑time employees are eligible for benefits including: 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.