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 is a remote position, open to candidates who reside in: Dallas, TX. 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: $196,733 - $258,212 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.
At Oscar, being an Equal Opportunity Employer means more than upholding discrimination-free hiring practices. It means that we cultivate an environment where people can be their most authentic selves and find both belonging and support. We're on a mission to change health care -- an experience made whole by our unique backgrounds and perspectives.
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.
Artificial Intelligence (AI): Our AI Guidelines outline the acceptable use of artificial intelligence for candidates and detail how we use AI to support our recruiting efforts.
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 ([email protected]) to make the need for an accommodation known.
California Residents: For information about our collection, use, and disclosure of applicants’ personal information as well as applicants’ rights over their personal information, please see our Privacy Policy.
Skills Required
- 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
- 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
- Experience translating regulatory developments into enterprise priorities, operating plans, and business controls
- 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
- 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
Oscar Health Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Oscar Health and has not been reviewed or approved by Oscar Health.
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Healthcare Strength — Employer-sponsored medical coverage for employees and their families with mental-health support is prominently offered. Wellness programming and digital care access add to perceived strength.
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Parental & Family Support — Paid parental leave of 10+ weeks, backup care, and family-forming support (including fertility and adoption benefits) are part of the package. Reproductive‑loss leave is also noted.
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Leave & Time Off Breadth — Multiple time‑off options, wellness days, and an unlimited vacation program for some roles are described. Paid holidays, paid sick time, and a long‑tenure sabbatical broaden time‑away choices.
Oscar Health Insights
What We Do
Health care is broken; we're trying to fix it. The Oscar team is focused on utilizing technology, design and data to humanize health care. We're a group of technology and health care professionals who looked at the current state of the US health care system, got frustrated by the horrible consumer experience, and decided to do something big about it. Backed by a renowned set of investors and advisors, we’ve set out to revolutionize health care.
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