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Medicare Advantage Expert

| Greater NYC Area

Hi, we’re Oscar. We’re a fully licensed health insurer. Our goal is to make healthcare simple, transparent, and human.

We are changing how health insurance works by creating a healthcare experience that’s intuitive and puts people, not cost or workflows, first. We’re using a consumer-focused and tech-driven approach to do so. This positions us uniquely in the space - and creates one of the biggest opportunities in healthcare.

We brought together leaders from top technology, service and healthcare companies to deliver on our promise and seize this opportunity. We all work side by side in a collaborative, energetic, and creative environment. The result: better people, better ideas, and better healthcare.

In this role, you are a cornerstones of our Medicare Advantage business. You will be key in designing our MA model and our go-to-market approach. In this, you will work directly executive leadership, the General Manager, and interact with all functions across Oscar.

This is an exciting opportunity to be at the forefront of growth at Oscar, helping enable our innovative model reach new members.

What is the position?

  • Strong exposure to all levels of the company and across all functions
  • Be THE knowledge expert on how MA works and how good MA organizations are run
  • Take responsibility substantial set of our go-to-market model & approach
  • Report directly to the General Manager
  • Likely many additional responsibilities that you’ll educate us on

Who are you?

  • You have Bachelor’s Degree or higher
  • You have 8+ years of MA experience and understand every aspect of what makes an MA organization great and what doesn’t
  • You have a million ideas that you were never able to put into practice
  • You are a critical thinker who can distill complex concepts and regulatory requirements into easily understandable action items
  • You are obsessed with getting the details right
  • You have an acute attention to detail and always strive for perfection when writing formal documents.
  • You get things done, even if it’s crunch time
  • You have passion for healthcare and a knack for making processes more systematic


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.

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