Associate Director, Site Reliability Engineering

Hi, we're Oscar. We’re hiring an Associate Director, Site Reliability Engineering 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 make health insurance simple, transparent, and human. We need your help to do so.

About this 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 in our people, our tools, and our processes so we can focus on solving big problems while learning from one another.

Oscar's business depends on trust. From forging relationships with our members through our Concierge teams to storing their Protected Health Information (PHI) in secure databases, a trust chain weaves through all that we do at Oscar. The Site Reliability Engineering team at Oscar is one of the crucial links in this chain; the infrastructural and platform layer decisions that we make impact the integrity, availability, and security of our services, and ultimately affect all interactions with members and providers.

You’ll manage a diverse and passionate team of builders and operators. We take pride in our ability to operate complex machinery and resolve incidents with a cool demeanor. You will help architect the systems from the ground up that are driving a new type of insurance company and ensure our site and critical services are always available. You’ll oversee the well being, success and personal growth of your team. 

You will report to the Senior Director of Infrastructure Engineering.

What you will actually be doing:

  • As a leader you will conduct the strategy and planning for your team operation
  • You will mentor your team members and nurture their career growth
  • You will be a key person in adaptation and tailoring of an agile process to help your team be productive and happy
  • You will contribute strong engineering skills and partake in design and implementation alongside your team members

The SRE team is responsible for:

  • Ownership and management of AWS infrastructure
  • Triage and help in resolution of a variety of requests coming from the rest of the organization
  • Guiding other organizational teams with a focus on automation, maintainability, and security
  • Measurement and monitoring of availability, latency and overall system health.
  • Engagement in capacity planning, demand forecasting, software performance analysis, and systems tuning.
  • Improvement and upkeep of documentation
  • Help with overall knowledge sharing across Oscar.

You at Oscar:

  • You put people first
  • You are passionate about mentoring people and team leadership 
  • You are hands-on and loving it
  • You care about operations.
  • You care about automation.
  • You’re passionate and open minded about technologies, but also mature enough to make the right choices when necessary. 
  • You can keep your cool while troubleshooting production issues.
  • You have at least 7 years of SRE or cloud software development and at least 3 years managing people

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 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 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.

Meet Some of Oscar Health's Employees

Whittney C.

Broker Support Representative Coach

Whittney’s job is to train, develop, and support broker support representatives. They are tasked with providing customer service to external brokers, who make up about 85% of Oscar’s enrollments.

Melissa C.

Concierge Operations Lead

Melissa coaches and manages concierge operations, which involves hiring, training, and developing the careers of her employees. She always ensures that her team has what they need to get the job done.

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