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Oscar Health // health insurance
New York City    Posted: Saturday, December 12, 2020
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Hi, we're Oscar. Were hiring an Associate Director to join our Technical Product & Program Office in our New York City location.

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 CTO Product & Program Office is a new team formed to help our Technology organizations achieve the benefits from clear organization, data-driven prioritization, & implementing consistent processes & standards.

As the Associate Director, Tech PMO, you will be responsible for building a team to assess the way Oscar runs its tech programs & processes today & identifying the way we should ultimately function for optimal scalability & long term growth & profitability. 

In partnership with the Director of CTO Product & Program Office, you will work with stakeholders across the company to evaluate, revamp, optimize, add to, & sometimes replace our current technology processes. Your job is to build a team to support this work & help increase our overall efficiency as a technology organization. 

You will report into a tech leader in the NYC office. 

Your organization will be responsible for: 

  • Providing Program & Project Management support for software implementation projects (both homegrown & 3rd party), strategic company initiatives impacting Tech, & Technical Product Launch.
  • Building visibility into reporting, status, & driving projects & programs to completion. 
  • Engineering & implementing consistent processes, standards, & engagement models across our technology teams.
  • Organizing regulatory audit & security activities within Tech engaging with various stakeholders throughout Oscar to remediate findings, produce evidence, maintain documentation, develop automations, & provide system walkthroughs in a timely manner. 
  • Partnering with our Technical Product Managers & the rest of Engineering, Infrastructure, & IT, Product, Insurance Operations, Data, Legal, Security, Sales, Marketing, & Finance to ensure we can support their overall success.


  • Help Oscar build technology processes & programs for scalable business growth.
  • Manage cross-functional work streams & initiatives for Tech projects, while always driving to clarify roles, responsibilities, & best practices for long term effectiveness.
  • Build a successful team to support this work & help increase our overall efficiency as a technology organization. 
  • Connect dots, build bridges, & link stakeholders to improve tech & business performance.
  • Create a culture of diagnosis & iteration. Ensure Oscar begins to systematically capture learnings & evolve how we do our work, to ultimately become a best-in-class insurance & tech operation.


  • 8+ years of experience in technology program or project management 
  • Experience with implementing & following Scrum & Agile principles
  • Experience leading cross-functional initiatives, including creating & implementing project plans/operational roadmaps & driving accountability
  • Experience working with & presenting information to leadership, tailoring communication as needed
  • Experience building successful teams at various levels
  • Experience establishing KPIs/metrics & using data to drive decision-making
  • Experience working with high-growth, fast-paced organizations
  • Comfortable with ambiguity, & willing to jump in & tackle problems & drive to resolution

Bonus points:

  • Healthcare experience
  • Consulting experience
  • Experience building structure in a growth stage startup
  • IT Audit or Compliance 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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