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Oscar Health // health insurance
Engineering, Full Time    New York City, United States    Posted: Monday, March 21, 2022
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Hi, we're Oscar. Were hiring a Director of Engineering to join our Engineering team. 

At Oscar, we are re-envisioning healthcare by bringing technologists & industry experts together. We believe that great technology can revolutionize the operations & infrastructure underlying todays healthcare & insurance systems, & is key to delivering transformative experiences for our members & the medical experts who provide their care. Oscar engineers work on some of the most challenging problems in tech helping users navigate the complex health industry through beautiful user applications, elegant distributed system design, making sense of noisy data, statistical learning, & language theory. We invest in our people, our tools, & our processes so we can focus on solving big problems while learning from one another.

About the role:

As the Director Engineering you will oversee the teams responsible for Oscars Member, Provider & Concierge facing applications on both web & mobile platforms. This position emphasizes extensive customer empathy, user centric design, deep collaboration with the Product & Data counterparts, Strategic Thinking & excellent people management. This is a critical role in the company since many of our major stakeholders experience the Oscar solutions through the software built in these teams. The quality of the software & the experience built in these teams directly impact Oscars success. We expect this person to be a force multiplier for the whole company.

You will report into the VP of Engineering. This is a hybrid role. You will work part of the time in the New York City office & part of the time work-from-home/remote. #LI-Hybrid


  • Strong focus on user centric design: The success of all our applications is directly dependent on the usefulness & experience for their respective audience. This person will bring metrics & analytics driven consumer level focus to strengthening the engagement & usability of our applications.
  • Long term technical strategy focused on innovation & velocity: This person will be able to contextualize & scale the architecture needs across multiple applications, identify patterns we need to invest in to ensure scalability, velocity of iteration & avoid future tech debt. E.g. We currently build our solution with React Redux & GRPC, this person will be able to help decide if we should move to GraphQL in an objective data-informed manner.
  • Excellent People Management: This team is composed of ~50 smart engineers with an hierarchical structure. This person will be responsible for maintaining high morale, high bar & providing scalable coaching & mentoring.
  • Deep cross functional collaboration: This is a highly strategic role with multiple company level initiatives in scope. This person will build strong relationships with all cross functional leaders & work collaboratively to build solutions that support the company objectives.
  • Continuously deepening industry knowledge/expertise: While existing healthcare industry knowledge is not a requirement, this person is expected to learn the space & become an expert over time.

You & your teams will be on call for the systems you own, but not the systems developed by other engineering teams - at Oscar, the team that builds it is the team that runs it.


  • You are passionate about analyzing & helping solve deep technical challenges, & share our fundamental belief that the proper application of technology & data are critical levers in transforming the US healthcare system.
  • You have 8+ years of software/frontend engineering experience, including end-to-end responsibility for complex & business critical applications.
  • You have deep experience with modern technologies, architectures & agile development methods, & are comfortable (excited by?) operating in complex, fast-moving environments.
  • You have 2+ years of people management experience & can effectively mentor senior leaders on management & technical tracks.
  • You have a track record of building high-functioning teams & can help us attract, develop, & retain the best engineering talent in the industry.
  • You make people & teams around you better through direct yet kind feedback, effective mentorship, & proactive collaboration.
  • You are neither territorial, nor build-an-empire oriented, but rather think, operate & lead toward doing what is best for the company. And you take your teams with you on that journey.
  • You understand the inclusion part of Diversity & Inclusion & can help us improve & maintain a great culture where the best ideas prevail, & everyone feels safe & heard.

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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