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Oscar Health // health insurance
Los Angeles, California, United States    Posted: Tuesday, August 10, 2021
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Hi, we're Oscar. Were hiring an Associate to join our Compliance team.

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:

Oscars Compliance Department manages & mitigates regulatory risk as we serve ever more members & clients across in ever more markets.  The Compliance Department also proves to our state & federal regulators & exchanges that we can fulfil our core regulatory obligations while providing members with higher-quality, lower-cost care.

As a Medicare Compliance Associate, you will focus on Compliance activity particular to Oscars Medicare Advantage (MA) line of business.  You will liaise with Oscars federal regulator, CMS, to ensure the compliant delivery of materials & services to MA plan members.  You will help set the standards for, & monitor the performance of, Oscars tech platform (called +Oscar) as it services Oscars own MA plans, as well as those offered by +Oscars clients & strategic partners.  

You will report to the Director of Medicare Compliance.


  • Support the Director of Medicare Compliance in preparing reports to the Boards of Oscars licensed insurance entities, maintaining Oscars relationship with CMS, & responding to audit & enforcement activities.
  • Provide MA-related advisory, investigatory, & remedial support services partnering with the Legal Department where appropriate to Oscars MA Product, Regional P&L, Insurance Operations, Clinical Services, Member Services, Sales, Finance, & Tech teams.
  • Digest regulatory updates from CMS & disseminate them to operational teams, tracking & where appropriate monitoring implementation.
  • Review MA marketing materials for adherence to applicable requirements before submitting them to CMS on Oscars behalf.
  • Prepare agendas, materials, & participants for regular Account Management calls with CMS.
  • Advise Compliance colleagues on the development of audit tools to assess MA compliance.


  • Bachelors Degree or equivalent work experience.
  • 4+ years experience in health plan (ideally MA) compliance, regulatory affairs, government affairs, or a similar field.
  • Experience with MA rules, including the Medicare Managed Care Manual & Prescription Drug Benefit Manual
  • Experience managing complicated projects, keeping track of details, & staging work to deliver projects on time.
  • Experience articulating regulatory requirements to business & technical staff to capture information & achieve results.
  • Experience with developing reporting & metrics.

Bonus points:

  • CHC, CCEC, or similar
  • Experience with HIPAA, data privacy, and/or data security processes
  • Prior experience working with regulators on compliance audits, reporting & other matters ideally in the MA space.
  • Experience in a TPA and/or start-up setting

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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