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Oscar Health // health insurance
New York City    Posted: Friday, August 14, 2020
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Hi, we're Oscar. Were hiring a Director, Regulatory Operations to join our Legal  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:

The Regulatory Operations team is a key part of the Oscar Legal team responsible for securing approval of Oscars plan portfolio via annual filings, drafting all Oscar insurance contracts, conducting regulatory research in support of the Legal, Government Affairs, & Regulatory Operations teams & securing approvals from regulators for expansion into new markets.

As Director, Regulatory Operations, you will be responsible for managing these functions & the team of ~12 professionals that discharges them. You will have primary responsibility for ensuring this team timely prepares, files & receives approval for all manner of regulatory documents & business initiatives.

You will work closely alongside other Oscar teams including Clinical, Finance, Risk, Legal, Network, Sales, & Marketing to ensure Oscars full regulatory readiness, & provide critical management oversight & leadership in the broader Legal organization. You will report into the General Counsel.


  • Provide management support & leadership with respect to the timely & accurate submission of Oscars annual regulatory obligations.
  • Provide management support & leadership with respect to the process for submitting new state insurance license applications & service area expansion applications.
  • Manage the provision of legal research to the Oscar Legal, Government Affairs, & the Regulatory Research & Approvals functions.
  • Manage, train, provide feedback & assign duties for manager direct reports to support their professional growth, management skills development, & ensure productivity, efficiency, & effectiveness in their roles.


  • Bachelor's Degree 
  • 8+ years of relevant healthcare insurance, regulatory affairs, or project management experience.
  • Experience building, managing & developing high-functioning teams 
  • Experience leading cross-functional initiatives at the organizational level

Bonus points:

  • Masters Degree or another advanced degree
  • Experience working with healthcare regulations & regulators 

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, unlimited 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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