Director, Systems Contracting

Oscar, New York

A better kind of health insurance company

At Oscar, we are working hard to provide the kind of health insurance we would want for ourselves. Our goal is to make health insurance simple, transparent, and human. We need your help to do so.

The Systems Contracting team is responsible for constructing and continuously improving Oscar’s hospital system agreements to ensure that our strategic vision, operational standards, and financial interests are reflected in our network partnerships.



In this role, you will collaborate with internal stakeholders (including leadership)  to understand Oscar’s business goals and regulatory requirements to drive the evolution of contracting strategies and land our most critical large system deals. You will also lead a deal team in managing a portfolio of active deals.


Your key responsibilities will be to:

  • Own the end-to-end lifecycle and operations of a portfolio of system deals-- from strategy development, to drafting proposals, to negotiation, to operational implementation hand-off.
  • Lead a deal team in analyzing and improving Oscar’s partnership terms and rate structures and leveraging your team’s insights from individual deals to refine our broader contracting frameworks.
  • Serve as the chief subject matter expert on your deal portfolio and a key internal knowledge resource on relevant market and policy developments.
  • Form strong working relationships with key internal stakeholders across the company and understand the impact of our contractual terms on their work streams and inform our network strategies.


About You:

Key components for success include:

  • 8+ years of work experience in the healthcare industry in a client-facing, leadership role
  • Direct experience with and a deep understanding of healthcare contracting, healthcare operations and market economics
  • A strong analytical background and the ability to quickly digest and evaluate complex financial structures and operational workflows, with a keen eye for detail
  • Ability to manage complex projects across the organization as well as to develop, motivate, and grow a team (including junior resources)
  • Strong leadership and other interpersonal skills needed to manage intricate negotiations and relationships and communicate clearly at the executive level
  • Capability to work within a standardized workflow while also being able to handle unforeseen problems, craft ad-hoc solutions, and leverage solutions to improve existing workflows


A plus, but not required:

  • An MBA or other professional degree from a competitive program with a clear track record of excellence
  • Experience with growth-stage enterprises and scaling departments and processes


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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