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Hi, were Oscar.

We are changing how health insurance works. Our goal is to make health insurance simple, transparent & human. We need your help to do so. We brought together leaders from top technology, service & healthcare companies to work side by side to disrupt health insurance. The result? Better people, better ideas, & better healthcare.

About the Role

As a Sr. 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 be responsible for managing offshore / nearshore teams of engineers.

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


  • Maintaining a standard set of tools & processes for teams to track cross-functional dependencies, deliverables, product/feature launches, & KPIs. 
  • Communicate 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. 
  • Identifying & problem-solving execution hurdles, especially across teams & cross-functional work streams.
  • Running retros when deadlines are missed, sharing lessons learned, & collaborating with teams to get back on track.
  • Manage external vendor relations
  • Perform as a functional bridge amongst external vendors as well as internal stakeholders.
  • Coordinate all vendor management tasks inclusive of working with external vendors & internal employees.
  • Ensure enterprise-wide needs for due diligence, risk assessment & continuing vendor monitoring are being accomplished.
  • Help & coordinate vendor processes & methods to approve vendors.
  • Ensure to track, measure, report & evaluate vendor performance.
  • Troubleshoot all vendor problems & present to management as required.
  • Identify improvement areas internally as well as perform closely with all internal stakeholders to prepare solutions.
  • Ensure to collaborate with IT areas to assure vendor partners effectively manage plus contracts are completely leveraged.

About You

  • 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 5 years of technical program management experience and is comfortable discussing the technical trade-offs in product development with engineers & product managers
    • Proficient knowledge of Agile methodology & Jira tool (must have)
    • Knowledge of SQL to perform data analysis (nice to have)
    • Knowledge of Software Test Life Cycle (STLC) (nice to have)
  • 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. Proven track record of 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.
  • A leader. Has led small teams of project or program managers helping to prioritize their work while still maintaining their own independent workload.

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.

COVID-19 vaccine requirements for in-person work: 

To protect the health & safety of our employees, we require any employee conducting in-person work* to be fully vaccinated against COVID-19 by their start date. If you are unable to be vaccinated due to medical or protected religious reasons, please reach out to our Benefits team at to submit an accommodations request.

*Note: In-person work includes: employees required to work from our offices, employees conducting sales work in the field & employees conducting at-home or in-person visits with members.

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