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Director of Plan Design

| Greater NYC Area

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.

The Commercial Plan Design Team is responsible for developing, coordinating, and executing a company-wide approach for designing Oscar’s insurance plans. Our plan designs define the coverage and features our members get, and at what cost. Our goal is to create plans that attract and retain members by providing the highest quality care, at the lowest cost. In this role, you’ll be a builder covering both strategy and operations, responsible for designing an innovative and competitive plan portfolio in collaboration with our Clinical, Sales, Marketing, Actuarial, Product, Network, and Regulatory teams and overall , creating a systematic approach for plan-related operations.


  • Market research: What plans and rates will be competitive in the marketplace? What perks and benefits make members happy? How do we highlight our networks and benefits through insurance plans?

  • Regulations: What regulatory constraints do we face? How should we innovate on our products whilst accounting for these regulatory constraints?

  • Risk and Data: How do our plans and pricing affect our insurance risk and change how members use care? How can we create products that route members to the most efficacious and cost-effective care?

  • Product Strategy and Design: How can we develop a deeper understanding of our target demographics? How are members using our current product? What plan features can we implement to make our plans more competitive to individuals and employers? How do we make plans that are simple to understand and communicate? How do we measure the success of our products?

About You: 

Your skills include:

  • Project management. You have experience managing complicated projects, keeping track of details, and staging work to deliver projects on time. You pay attention to details.

  • Product strategy. You are a critical thinker who can take vague ideas and complex constraints into implementable products. You can identify new opportunities that move the needle. You collect and leverage data to clarify decisions whenever possible.

  • Analytics. You think in a structured and systematic way. You are super comfortable working with data, spreadsheets, and charts. This comes from a background in finance, economics, or data science.

  • Creativity. You have distinct ideas, but can quickly organize your thinking into frameworks and coherent strategies. You find it easy to distill complex topics into simple explanations. You love finding elegant solutions in a world full of complicated constraints.

Key components for success include:

  •  7+ years of work experience working in economics, strategic finance, pricing, data science or related field

  • Direct experience working in the health insurance pricing, actuarial or related area within the healthcare industry

  • A strong analytical background and the ability to quickly digest and evaluate complex financial structures, with a keen eye for detail

  • Ability to manage complex cross-functional projects across the organization

  • A proven leader with a track record of building strong teams

  • You get things done, even if it’s crunch time

  • You have passion for healthcare and a knack for making things 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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295 Lafayette St, New York, NY 10012