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Chief of Staff to Chief Insurance Officer

Oscar Health

Oscar Health

People & HR, Operations
New York, NY, USA
Posted on Tuesday, May 16, 2023

Hi, we're Oscar. We're hiring a Chief of Staff to the Chief Insurance Officer to join our Executive Office team.

Oscar is the first health insurance company built around a full stack technology platform and a focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role

As the Chief of Staff to the Chief Insurance Officer, you’ll work with InsureCo leadership to build, scale and run Oscar’s Insurance business as we drive to meet our strategic goals. You’ll also work with leaders across the company, including Chief of Staff roles for other executives, to solve complex problems, drive solutions, and orchestrate operational initiatives.

A successful candidate can work independently and is a tight operator who can run the CIO’s "business office" processes (objectives and key results, workforce planning, etc) and work closely with the CIO to develop strategic solutions to address market dynamics and achieve corporate goals. They should be able to wrangle senior leaders across the Insurance business and drive them to act as a collective “operating committee” that solves business problems and makes business decisions in a unified way. They can “keep an eye” on the Insurance business’ day to day operations and provide the CIO with executive-level updates. Lastly, they’d have the business acumen and strategic thinking abilities to act as a thought partner for the CIO and the Insurance business’ business line and regional leaders.

You will report to the Chief Insurance Officer. This is a hybrid role. You will work part of the time in the New York City office and part of the time work-from-home/remote. #LI-Hybrid

The base pay for this role in the state of New York is: $176,000 - $231,000 per year. You are also eligible for employee benefits, participation in Oscar’s unlimited vacation program, company equity grants and annual performance bonuses.


  • Act as a proxy for the CIO to work through strategic level issues
  • Facilitate cross departmental processes in partnership with SMEs (i.e., performance management, budget reporting) and drive efficiency by prioritizing time spent on high-value work
  • Drive departmental efficiencies through process improvements and personnel reallocations
  • Provide leverage. Rank competing priorities and create decision-making frameworks that help prioritize critical tasks for the CIO and their ‘business office’
  • Provide program leadership on critical InsureCo and cross-functional efforts; Lead cross-functional issues that need to be driven to resolution
  • Support the CIO by leveraging their responsibilities, including:
    • Attend meetings / calls on their behalf
    • Ensure CIO is prepared for meetings, with appropriate pre-reads and context
    • Drive staff/operating committee agendas to ensure smooth running of the organization and thoughtful discussion on key topics
    • Manage preparation for and execution of governance meetings owned by the CIO
    • Aggregate, evaluate, and track InsureCo’s vitals and KPIs
    • Partner with the People Team to drive staff development across the organization


  • BA/BS Degree or equivalent experience required
  • 12+ years of professional experience
  • Experience partnering with executive leaders and working cross-functionally
  • Experience working within a rapidly scaling organization

Bonus Points

  • 8+ years of program management experience, preferably in the insurance industry
  • Business financial acumen; managing and running a budget

This is an authentic Oscar Health job opportunity. Learn more about how you can safeguard yourself from recruitment fraud here.

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..

Pay Transparency:

Final offer amounts, within the base pay set forth above, are determined by factors including your relevant skills, education, and experience.

Full-time employees are eligible for benefits including: medical, dental, and vision benefits, 11 paid holidays, paid sick time, paid parental leave, 401(k) plan participation, life and disability insurance, and paid wellness time and reimbursements.

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.