Senior Director, Enterprise Compliance

Oscar Health•New York, NY

3d•$218,592 - $286,902•Hybrid

About The Position

Oscar is hiring a Senior Director, Enterprise Compliance to support the execution and continuous improvement of its enterprise compliance program. Reporting to the Vice President, Chief Compliance Officer, this role provides leadership over regulatory compliance, regulatory change management and implementation, compliance operations, investigations, monitoring and auditing, policy governance, and compliance education. The position anticipates regulatory and industry developments, translates them into enterprise priorities, and partners with cross-functional leaders to identify and mitigate compliance risks, strengthen internal controls, and promote ethics and integrity. It exercises significant independent judgment, develops the compliance organization, and serves as a trusted advisor to business leaders on complex healthcare regulatory matters. The position is based in Oscar’s New York City office and follows a hybrid schedule requiring three in-office days per week. Thursday is a required in-office day; the other two office days are flexible. Base pay is $218,592–$286,902 per year. The role is also eligible for employee benefits, unlimited vacation, company equity grants, and annual performance bonuses.

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, including experience presenting to executive leadership, governance committees, regulators, or external auditors.

Nice To Haves

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.

Responsibilities

Lead execution and continuous improvement of the enterprise compliance program, including multi-year strategy, annual work plans, risk assessments, policy governance, regulatory change management and implementation, monitoring, auditing, and reporting.
Translate enterprise compliance priorities into operating plans; 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 potential effects on products, market participation, business strategy, and the 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 concerns.
Partner with Legal, Privacy, Security, Internal Audit, Enterprise Risk, Clinical, Product, Operations, and People teams to embed compliance requirements into business processes and strategic initiatives.
Lead education, communications, and awareness initiatives that strengthen Oscar’s culture of ethics and compliance, and uphold enterprise standards.
Lead compliance reporting and engagement for executive leadership, the Compliance Committee, Board committees, and regulatory examinations; support interactions with regulators and external auditors.
Comply with all applicable laws and regulations.
Perform other duties as assigned.