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Senior Director, Enterprise Compliance

Oscar Health - Remote - Remote - posted 2026-09-15

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Salary: USD 196,733 - 258,212 / annual

Oscar Health is seeking a Senior Director, Enterprise Compliance to lead the execution and continuous improvement of the company's enterprise compliance program. Reporting to the Chief Compliance Officer, this role provides leadership over key compliance functions including regulatory compliance, regulatory change management and implementation, compliance operations, investigations, monitoring and auditing, policy governance, and compliance education. Key responsibilities include: - Lead execution and continuous improvement of Oscar's enterprise compliance program, including multi-year compliance strategy, annual work plans, risk assessments, policy governance, regulatory change management, monitoring, auditing, and reporting. - Translate enterprise compliance priorities into operating plans; establish ownership and governance; allocate resources; develop compliance managers and team members; and drive accountability for measurable outcomes. - Anticipate regulatory and industry developments and advise senior leaders on 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. - Oversee compliance investigations, hotline reporting, Special Investigations Unit, fraud-prevention activities, corrective action plans, and remediation efforts with timely resolution and appropriate escalation. - 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 through education, communications, and awareness initiatives. - Lead compliance reporting and engagement for executive leadership, Compliance Committee, Board committees, and regulatory examinations; support interactions with regulators and external auditors. Oscar is a technology-enabled health insurance company founded in 2012, focused on serving members through a full-stack technology platform and relentless focus on customer experience. 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 QUALIFICATIONS: - 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.

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