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Hi, we're Oscar. Were hiring an Executive Assistant to join our team in our New York office. 

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.

Running efficient operations is a key factor to a successful organization. This Executive Assistant will be supporting our CIO & CFO to strategically manage their time & priorities to best support & enable success. This position requires someone who loves details & can connect them to the bigger picture, can roll with the punches, & loves the challenge of working in an ever-changing & growing environment!  You must be a team player & be able to thrive in a start-up & busy culture.

About the role:

You will support our CIO & CFO to ensure that their organizations are fully supported by accomplishing the following:

  • Proactively manage their calendars
  • Coordinate meetings & conference calls & reserve locations.
  • Keep a pulse on team culture & morale -- bubble up issues with ideas for solutions.
  • Triage workflow for the leaders; develop an understanding of task & issue priorities; bring urgent matters to attention.
  • Draw on experience & judgment while handling highly confidential & proprietary matters.
  • Prepare travel arrangements & submit expense reports in a timely manner.
  • Greet guests & make them comfortable when they arrive with professionalism & poise.
  • Partner with colleagues for meeting planning & assist with special projects as needed.


  • Bachelors degree 
  • 3 years of experience in a fast-paced office environment supporting a C-level executive
  • Experience working with discretion & tact in handling highly confidential & sensitive information.

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 encourage our members to care for their whole selves, & 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, & 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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