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Oscar Health // health insurance
Design, Full Time    New York City    Posted: Tuesday, December 15, 2020
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Hi, we're Oscar. Were hiring a Health Insurance Plan Design Associate to join our Health Insurance Plan Design team.

Oscar is a technology-driven, consumer-focused health insurance startup founded in 2012 & headquartered in New York City. Our goal is to make health insurance simple, transparent, & human. We need your help to do so.

About this role:

You will be responsible for plan portfolio development & management, supporting Oscars Small Group markets.  Responsibilities will include the development of market-specific health insurance plan portfolios, identifying enhancements, & differentiating capabilities to meet the needs of Small Group employers & their employees.  You will serve as the Subject Matter Expert throughout the health insurance plan management & implementation processes.  The successful candidate has a strong background in small group healthcare strategy, plan design/product development, implementation & experience working cross-functionally. This is an opportunity to be part of Oscars growth & commitment to improving our Small Group experience.

You will analyze & synthesize external data (e.g., competitor, enrollment, & market trends) & internal metrics (e.g., financial targets, membership targets, customer pain points, etc.) by region.  You will collaborate with Sales, Marketing, & Actuarial teams to develop plan design strategies.  You will develop the regulatory documents (e.g., Schedule of Benefits, Summary of Benefits & Coverage) required for regulatory filings.

In this role, you will report to the Insurance Plan Portfolio Sr. Manager. 


  • Conduct detailed competitive analysis & synthesize information for different internal stakeholders.
  • Maintain a comprehensive understanding of external & internal influences & competitive pressures to develop & enhance product portfolios.
  • End-to-end small group product decisions for growth & financial impact with compliance & regulatory focus.
  • Manage product lifecycle activities, including development, implementation, & market rollout.
  • Serve as subject matter expert for plan design, benefits, & cost share information.  Document & maintain sources of truth of plan design details.
  • Develop regulatory plan documents required for regulatory filings.


  • 5+ years managing health insurance plan portfolios; commercial health insurance experience.
  • Strong sense of urgency & a bias for action; you thrive in fast-paced environments.
  • Strong ability to influence others without direct authority.
  • Strong interpersonal interactions (e.g. partnering, consulting, etc.) & open to giving/receiving constructive feedback.

Life at Oscar: 

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 & find both belonging & support. We're on a mission to change health care -- an experience made whole by our unique backgrounds & perspectives.

We aim to make health care affordable & accessible for all, & apply this same vision to our perks & benefits, including: medical benefits, unlimited paid-time off, paid parental leave, retirement plans, company social events, stocked kitchens, wellness programs, & volunteer opportunities.

Reasonable Accommodation:

Oscar applicants are considered solely based on their qualifications, without regard to applicants disability or need for accommodation. Any Oscar applicant who requires reasonable accommodations during the application process should contact the Oscar Benefits Team ( to make the need for an accommodation known.

Pay Transparency Policy:

Oscar 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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