Regulatory Counsel, Medicare

Oscar, New York

A better kind of health insurance company

Hi, we’re Oscar.

We are changing how health insurance works. Our goal is to make health insurance simple, transparent and human. We need your help to do so. We brought together leaders from top technology, service and healthcare companies to work side by side to disrupt health insurance. The result? Better people, better ideas, and better healthcare.

As Regulatory Counsel, Medicare, you will be a key member of the Legal and Compliance teams responsible for providing leadership and guidance for the compliance of the applicable regulation as Oscar prepares to launch its Medicare Advantage business in 2020. You should be comfortable in an ever changing environment as we continue to grow!

We currently operate in commercial markets in New York, New Jersey, California, Texas, Ohio and Tennessee.


Deliverables: What you have to achieve

  • Provide legal guidance and advice to Oscar’s business on a range of Medicare Advantage regulatory matters, including claims payment and adjudication, provider contracting, anti-fraud, utilization review, complaints, provider payment disputes, and others.
  • Design and oversee operational initiatives to comply with state and federal statutory and regulatory requirements applicable to Oscar’s Medicare Advantage business
  • Prepare, advise and/or manage regulatory filings, licensing and reporting requirements
  • Support cross-training, problem-solving, and knowledge development across Oscar to support Oscar’s entry into Medicare Advantage
  • Advise and investigate regulatory and industry development, including identification and assessment of regulatory risks and the ongoing monitoring, tracking of relevant regulatory proposals
  • Draft policies and edit existing policies to ensure Oscar’s compliance with applicable state and federal law
  • Closely partner and interact with federal and state regulators and government agencies

About You:

  • J.D. from an ABA accredited law school with 7+ years of legal experience
  • 5+ years of experience in a Medicare Advantage compliance or regulatory role at a Medicare Advantage plan, or comparable experience.
  • Highly organized, detail oriented, collaborative team player, who thrives in a dynamic fast-paced environment
  • Ability to manage competing demands, shifting priorities and interests of multiple stakeholders
  • Demonstrated ability to take ownership with strong work ethic and follow-through skills
  • Excellent leadership and communication skills to drive results across a wide range of stakeholders, from data scientists to sales executives to external consultants.



At Oscar, being an Equal Opportunity Employer means more than upholding discrimination-free hiring practices. It means that we work to cultivate an environment where exceptional people can be their most authentic selves and find both belonging and support. We're on a mission to change healthcare -- an experience made whole by your unique background and perspectives.

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.

Pay Transparency Policy: Oscar's Pay Transparency Policy ensures that you won't be discharged or discriminated against based on whether you've inquired about, discussed, or disclosed your pay. Read the full policy here.


About Oscar

Founded in 2012, Oscar is probably the last thing you would expect from a technology startup – a seemingly old-fashioned healthcare insurance provider. The company provides clients with the kind of clarity and simplicity we have come to expect from an e-commerce site. And, of course, they're hiring.

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Want to learn more about Oscar? Visit Oscar's website.