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Oscar Health // health insurance
New York City, United States    Posted: Tuesday, June 23, 2020
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Hi, we're Oscar. Were hiring a Director to join our Business Operations 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 this role:

The Operations team builds, runs, & optimizes all functions of Oscars core business. Business Operations takes a macro view of Operations in the context of the broader company, & aims to help the company work most effectively & scale.

As a leader at the company & within the Operations team, you will be responsible for assessing the way Oscar runs its business today & identifying the way we should ultimately function for optimal scalability & long term growth & profitability. As such, you will partner with leaders across the company to evaluate, revamp, optimize, add to, & sometimes replace our core business functions. Your job is to ensure Oscar is able to scale first to the point of profitability & then ultimately to longevity as a major player / disruptor in the healthcare space. Youll report into the VP, Business Operations.


  • Help Oscar build frameworks for scalable business growth
  • Analyze the picture of the near & long term ROI across our major bets as a company & make recommendations to executive leadership on strategy decisions
  • Partner with other business leaders to drive decisions around Oscars consumer offering, & stand up the teams/processes to take offerings to market YoY
  • Connect dots, build bridges, & link leaders to ensure all company leaders are armed with the information to do their jobs excellently & held accountable to managing towards Oscars operational & financial goals
  • Drive the alignment of cross-functional work streams & initiatives to clarify roles, responsibilities, & best practices
  • Create a culture of diagnosis & iteration; ensure Oscar systematically captures learnings & evolves how we do our work, to become a best-in-class insurance & tech operation
  • Partner with Finance team to iterate on company processes for budgeting & strategic planning, understanding constraints around tech & business requirements
  • Serve as a general athlete & deployable resource to jump into any business issue & help right the ship


  • 8+ years of experience developing & scaling organizations in business operations, consulting or advisory roles
  • Experience working with & advising executive leadership
  • Experience leading cross-functional initiatives from ideation to completion
  • Experience using a combination of qualitative inputs & quantitative data to drive decision-making
  • Experience with high growth businesses

Bonus points:

  • Technology industry experience
  • Healthcare experience

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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