Oscar Insurance is hiring a

Sr. Director, Operations Financial Management

New York, United States

Hi, we're Oscar. We’re hiring a Sr. Director, Operations Financial Management to join our Business Finance team in our New York office. 

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.


  • Drive business plan development and insight into the economics of business to drive profitable growth and operating efficiency focused on long-term value creation.
  • Lead and manage a financial management and performance management framework to allow us to better manage the operational functions, technology business at a granular level.
  • Develop, monitor and refine a limited number KPIs required to steer the operational, technology and new business and evaluate performance
  • Evaluate capital funding levels based on the opportunities presented in the regions and prioritize allocations based on potential risk-adjusted returns of the projects and funding constraints of the company.
  • Establish external and internal benchmarks to help advise and challenge key stakeholders to drive improvements in their areas of responsibility
  • Lead business FP&A and reporting responsibilities for Oscar operational functions and Tech-Co.


  • 10+ years of work experience, and a strong leadership and client-facing background in finance roles in the healthcare or technology industries.
  • 5+ years of work experience in financial planning, commercial finance, and accounting at a financial institutions (banking, lending, etc)
  • In-depth understanding of the business combined with seasoned judgment and experience
  • Executive presence and ability to communicate with, influence, and manage stakeholders, including C-level executives

Bonus points:

  • Experience working in fast paced start-up or technology industry is also preferred
  • Degree in Finance or Accounting; MBA preferred

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 ([email protected]) 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.