Events  Deals  Jobs 
    Sign in  
Oscar Health // health insurance
New York City, United States    Posted: Thursday, February 25, 2021
Apply To Job

Hi, we're Oscar. Were hiring a Director of Medicare Compliance to join our Compliance 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.

About the role:

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

As Oscars Director of Medicare Compliance, you will be responsible for all Compliance activity particular to Oscars Medicare Advantage (MA) plan offerings.  In cooperation with the Director of Corporate & Commercial Compliance, you will ensure that Oscars company-wide Compliance Program identifies & addresses regulatory risk.  As Oscar increasingly offers its technology platform to other insurers, you will also help build a replicable model for ensuring that Oscars support for their MA plans is seriously & demonstrably compliant.

You will report into the Vice President of Compliance.


  • Lead a new Medicare Compliance team in performing (and in ultimately evaluating & redesigning where appropriate) all Compliance functions including monitoring, internal & external audits, & reporting specific to Oscars MA line of business.
  • Deploy these functions replicably & consistently to support Oscars technology as it services new & existing MA clients & strategic partners.
  • 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.
  • In collaboration with the Legal & Government Affairs functions, manage Oscars relationship with CMS as it pertains to the MA line of business, in order to facilitate tech-driven innovation, remediate identified noncompliance, & meet or exceed Compliance Program Effectiveness requirements.
  • Coordinate Oscars response to all MA-related reporting & regulatory (CMS or contracted) audit obligations, driving year-over-year improvement across all content-generating teams.
  • Work with others in the Compliance Department (including the Corporate & Commercial Compliance team), & with the other parts of Oscars Risk & Controls function, to manage regulatory risk sustainably but with a relentless focus on growth & innovation.
  • Structure & refine internal reporting & monitoring processes, enabling Oscars corporate boards to fulfill their commercial-side compliance & delegate oversight responsibilities.
  • Drive productive, longer-term changes that lead Oscars Medicare compliance activities to meet or exceed industry standards for insurers, tech innovators, & public companies.


  • College degree
  • 9+ years experience in a healthcare compliance setting, including managerial & MA experience
  • Knowledge of federal laws & regulations, & CMS sub-regulatory guidance & rules, applicable to MA plans
  • Fluency with CMS Program Audit, 1/3 Financial Audit, Annual Reporting, Medicare Data Validation, & other CMS oversight activities
  • Experience preparing & delivering reports to boards of directors in a for- or not-for-profit setting
  • Experience building collaborative relationships across internal functions & with external (strategic & regulatory) stakeholders
  • A history of producing timely & accurate deliverables to internal & external parties while managing competing priorities
  • Experience providing tactical & strategic advice & identifying the need for, & delivering, education & training to support compliant product growth
  • Proven success in building, developing, & advocating for a team

Bonus points:

  • CHC, CCEC, or similar
  • Operational or internal audit experience
  • Experience in a start-up and/or health tech environment
  • Experience preparing & delivering reports destined for a public company board
  • Experience in a TPA 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 aim to make health care affordable & accessible for all, & apply this same vision to our perks & benefits, including: 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.

Apply To Job
© 2021 GarysGuide      About    Feedback    Press    Terms