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Oscar Health // health insurance
Engineering, Full Time    Remote    Posted: Wednesday, September 22, 2021
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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.


As the VP, Engineering Concierge & Member Experience you will be responsible for the teams & systems ranging from AuthZ/AuthN, Population health management to the mobile & web applications that power our unique member experience. Your primary responsibility will be to manage & evolve an already world class engineering team & tech stack. As part of Oscars leadership team, you will partner & align your teams around business decisions & ensure we are operating on the right vision, strategy, & roadmaps to solve our most pressing problems. In addition, you will manage roadmaps, timelines, & overall execution in your organization; ensure smooth cross-team & cross-departmental collaboration; & ensure consistent performance management.

Sample projects the application teams are tackling:

  • Virtual Care. At Oscar we believe that an amazing telemedicine experience is a key ingredient in both lowering costs & providing the best experience possible for our members, & this is reflected in utilization that is 8X that of our competitors. We are constantly working to improve & extend our virtual care platform, as we expand its use from urgent & episodic care toward a longitudinal replacement for primary care for our members.

  • Search & Scheduling. Oscar members can search for doctors, medical conditions, drugs, & facilities based on a variety of criteria, & can even schedule doctor appointments using our web & mobile applications.

  • Member Experience. Our web & mobile apps not only help our members access care & keep up with their insurance information, they are also a key channel of communication between us & our members. We use these channels to nudge better engagement with their providers, better management of their chronic conditions etc there by directly impacting health outcomes.

  • Supporting Member Services. Its not just about the technology for personal matters such as healthcare, a human touch is often better than the most sophisticated software. We invest heavily in creating software to help our Concierge member service teams do their jobs ever more effectively.

About You:

  • 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 15+ years of software engineering experience, including a proven record of successful leadership.

  • You have deep experience with modern technologies, architectures & agile development methods & an extensive track record of driving innovation in fast-paced environments.

  • You have 8+ 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.

  • The Concierge & Member Experience group is approximately 50-70 engineers. Were looking for someone who has experienced that scale & growth rate to help us build the team successfully while continuing to enhance our approach to work.

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 (either full-time or part-time), employees conducting sales work in the field & employees conducting at-home or in-person visits with members.

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