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Oscar Health // health insurance
Remote    Posted: Thursday, August 05, 2021
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Hi, we're Oscar. We're hiring a Technical Program Manager to join our team in our NYC 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. And we need your help with that.

As a Technical Program Manager, you will work closely with Product, Engineering, & Business teams to support planning & rollout of our technology products within a fast-moving, rapidly growing technology organization. 

You will report into a PMO Tech Leader. This is a remote role, you will work remotely in one of the following states: Arizona, California, Connecticut, Florida, Georgia, Illinois, Maryland, Massachusetts, Michigan, New Jersey, New Mexico, New York, North Carolina, Ohio, Pennsylvania, Rhode Island, Tennessee, Texas, Utah, Virginia, or Washington. Note, this list of states is subject to change.


  • 5+ years relevant work experience in program management with product, programs, or engineering focus.
  • A fast learner. Able to grasp complex concepts, is curious by nature & asks questions to quickly understand content areas. 
  • Comfortable with complex systems. Knows how to analyze & decompose a complex system & how different systems interact. 
  • Technical experience. Has worked in a tech organization in the past & is comfortable discussing the technical trade-offs in product development with engineers & product managers. Experience working in a technical domain is preferred.
  • A strong communicator. Understands what level & form of communication to use to keep your team, stakeholders, & leadership in alignment.
  • Very organized. Has project management experience using both waterfall & Agile frameworks & is comfortable with coordinating across multiple teams to build a centralized understanding of the overall efforts status & keep teams on track.
  • Detail & process oriented. Identifies opportunities to improve & scale how teams work.
  • Collaborative. Loves helping engineers, data scientists, operations experts, & other team members do their best work.
  • Open-minded. Is flexible, positive, comfortable with ambiguity, & most importantly willing to jump in & tackle problems.
  • Analytical. Knows how to read between the lines, connect the dots, & quickly identify opportunities & risks.
  • Independent. Can identify key areas for focus & prioritize work effort on a regular basis while communicating to the Associate Director, Tech PMO.


  • Building & maintaining a standard set of tools & processes for teams to track cross-functional dependencies, deliverables, product/feature launches, & KPIs. 
  • Supporting the building & implementation of standards in tools like & Jira.
  • Communicating regularly with technology teams to track progress, surface deadlines for deliverables, understand risks, & facilitate conversations to mitigate these risks.
  • Sharing updates on progress, risks, etc. with impacted teams, tech leadership, & counterparts at Oscar
  • Developing a deep understanding of the product, platform domains, architecture, integrations, stakeholders (including their roles & responsibilities), cross-project dependencies, & timelines. 
  • Running retros when deadlines are missed, sharing lessons learned, & collaborating with teams to get back on track.
  • Conducting interviews to gather customer requirements via workshops, questionnaires, surveys, site visits, workflow storyboards, use cases, scenarios, & other methods.
  • Identifying & establish scope & parameters of requirements analysis on a project-by-project basis to define project impact, outcome criteria, & metrics
  • Working with stakeholders & project team to prioritize collected requirements..
  • Translating conceptual customer requirements into functional requirements in a clear manner that is comprehensible to developers/project team.

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 applicant's 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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