Director, Engineering Effectiveness

    • New York, NY

Hi, we’re Oscar. We’re hiring a Director of Engineering Effectiveness to join our Engineering team in our New York City office.

Oscar is a technology-driven, consumer-focused health insurance startup founded in 2012 and headquartered in New York City. Our goal is to refactor the healthcare industry and make health insurance simple, transparent, and human. We need your help to do so.

About the role:

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, and language theory. We invest our people, our tools, and our processes so we can focus on solving big problems while learning from one another.

Engineering Effectiveness is one of three infrastructure groups at Oscar. If Site Reliability Engineering is infrastructure-as-a-service, then think of the Engineering Effectiveness group as platform-as-a-service. We build and operate platform services such as schedulers, consensus services, monitoring and common/shared engineering services for Oscar’s software engineers to use. In addition, we educate and train the engineering organization on best practices, we build codelab tutorials, implement frameworks and provide common libraries.

As the Director of Engineering Effectiveness, you will begin with managing two teams - Engineering Effectiveness and Data Infrastructure - and report into our Senior Director of Infrastructure Engineering.

What you will actually be doing:

  • As a leader you will conduct the strategy and planning for your teams’ operations
  • You will mentor your teams’ members and nurture their career growth
  • You will be a key person in adaptation and tailoring processes to help your teams’ be productive and happy
  • You will contribute strong engineering skills and partake in design and implementation alongside your teams’ members

You at Oscar:

  • You are passionate about mentoring people and team leadership
  • You put people first and care about the development of your teams and the effectiveness of your teams
  • You care about platforms and automations
  • You can work well under pressure and within tight deadlines
  • You have at least 10 years of Platform or SRE development and at least 5 years managing people
  • You enjoy working and deploying technologies such as schedulers, data streaming, containerization and observability in Python and Go or other similar technologies

Life at Oscar:

At Oscar, being an Equal Opportunity Employer means more than upholding discrimination-free hiring pracrices. It means that we cultivate an environment where people can be their most authentic selves and find both belonging and support. We’re on a mission to change health care -- an experience made whole by our unique backgrounds and perspectives.

We encourage our members to care for their whole selves, and 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, and volunteer opportunities.

Reasonable Accommodation:

Oscar applicants are considered solely based on their qualifications, without regard to the applicant's disability or need for accomodation. 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.

Oscar is a technology-focused health insurance company.

Oscar Health Company Image

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