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Oscar Health // health insurance
Engineering, Full Time    New York City    Posted: Tuesday, December 29, 2020
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Hi, we're Oscar. Were hiring an IT Engineer to join our IT team in our New York City 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.

About the role:

We are growing rapidly, & building most everything from scratch on Mac, Linux, & Chrome OS. The ideal candidate will be someone who enjoys building & supporting systems with automation & security in mind, takes ownership of support, as well as provides cross-support for other Oscar offices.


  • Develop a deep understanding of Oscars internal IT function, while also recommending & implementing improvements
  • Interject yourself throughout the organization to increase efficiency through technical solutions
  • Scale technical infrastructure to accommodate rapidly growing end-user counts
  • Drive exceptional end-user support & increase self-service


  • 3 years supporting large environments of Mac & Chrome OS users with an ability to patiently troubleshoot issues while helping educate end users.
  • Experience with inventory control & provisioning laptops.
  • Up to date knowledge about the latest tools & methods for managing these environments
  • Ability to design & troubleshoot wired & wireless networks
  • Building with redundancy & fault tolerance as a priority
  • Proficient in Atlassian suite (Jira & Confluence)
  • Ability to architect new systems to help ease day to day operations
  • You love owning things: youre proud of the things you build & thrive with responsibility
  • Experience with AWS is essential.
  • Experience with Cisco & Meraki networking gear is essential
  • Experience with APC UPS & PDU infrastructure is a plus
  • Experience with call centers or phone systems (IVR troubleshooting)
  • Experience with Single Sign On

Bonus points:

  • Experience with Google Apps for Work
  • Experience with Casper Suite

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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