Regional Market Leader

Hi, we're Oscar. We’re hiring a Regional Market Leader to join our Network team.

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

About this role:

The Market P&L Group is responsible for overseeing and maximizing risk-adjusted profitability across Oscar’s book of business. As leader of a region for our Market P&L Group, the Regional Market Leader will maintain and oversee 9-10 digits’ worth of premiums, generated from tens of thousands to hundreds of thousands of members. They will ensure we achieve critical financial targets and work with stakeholders across the company to drive growth, profitability, and quality member and provider experiences with Oscar. Furthermore, the Regional Market Leader will ensure that our strategic vision and financial interests are reflected in the networks we build, while continually improving our existing operations, so we can continue on our path of establishing Oscar as a nationally trusted brand in healthcare. 


As Regional Market Leader, you will collaborate with internal and external stakeholders and leaders to understand Oscar’s business goals and regulatory requirements, drive the evolution of our business strategies, and shape our most critical hospital system deals. You will oversee a deal team focused on developing hospital executive relationships within Oscar’s expansion markets, negotiating a portfolio of active deals, and ensuring that your Regional team is aligned toward maximizing risk-adjusted profitability.

Your key responsibilities will be to:

  • Shape, maintain and oversee the business plan for your market (i.e., 9-10 digits’ worth of premiums generated from tens of thousands to hundreds of thousands of members).
  • Generate financial insights that will ensure Oscar’s long-term sustainability, and work with internal departments and leaders to execute on these insights. 
  • Develop and maintain relationships with key hospital system leaders and oversee high-level transactions within your market.
  • Ensure a high-quality Oscar experience for members and providers.
  • Incorporate new product lines and grow existing product lines. 
  • Ensure a high standard of excellence for both expansion and existing operations within your market.
  • Serve as a senior ambassador across the company and externally for Oscar’s commercial interests. 

About You:

Key components for success include:

  • 10+ years of work experience, prior P&L responsibility, and a strong leadership and client-facing background. Preference for experience in the healthcare industry.
  • Track record of successfully managing business units and economic drivers with a multi-year trajectory; particularly identifying and transforming key healthcare financial drivers.
  • A strong financial/analytical background, and the ability to quickly digest and evaluate complex financial structures and large amounts of data in order to make commercially intelligent business decisions. 
  • Executive presence and ability to communicate with and lead presentations for senior leaders, including C-level executives both internally and externally. 
  • Strength in negotiations involving complex economics and communication thereof with internal and external stakeholders.
  • Orientation towards designing processes systematically while being able to execute quickly within a fast-paced, fluid and goal-oriented environment.

A plus, but not required:

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

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

We encourage our members to care for their whole selves, and we encourage our employees to do the same with comprehensive medical benefits, generous paid-time off, paid parental leave, retirement plans, company social events, stocked kitchens, wellness programs, and volunteer opportunities.

Reasonable Accommodation

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 ( 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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