VP, Engineering: Platform

Oscar, New York, NY

A better kind of health insurance company

At Oscar, we are re-envisioning healthcare by bringing technologists and industry experts together. We believe that great technology can revolutionize the operations and infrastructure underlying today’s healthcare and insurance systems, and is key to delivering transformative experiences for our members and 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, 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.



As the VP, Engineering — Platform, you will oversee the teams responsible for our core data systems and the logical services that define our fundamental business processes. Your primary responsibility will be to grow and lead a world class engineering team, and ensure they have everything they need to be successful. As part of Oscar’s leadership team, you will inform and align your teams around strategic decisions and ensure we are operating on the right vision, strategy, and roadmaps to solve our most pressing problems. In addition, you will manage roadmaps, timelines, and overall execution in your organization; ensure smooth cross-team and cross-departmental collaboration; and ensure consistent performance management.


Sample projects the platform teams are tackling:


  • Provider data and network intelligence. Provider data represents our most complex ETL pipeline and classical problems abound — missing, invalid, and incorrect data; reconciliation of conflicting data across multiple sources; need for both batch and online updates; “fuzzy” entity matching; confidence measurement; quality signal development; recommendations; etc. We are building a high-quality national provider database and the tooling for managing and evaluating our networks on top of a clean data store.
  • Claims Processing. We are in the midst of building and incrementally rolling out a new claims processing system that will drive scalable business processes as well as innovative product development. This is a multi-year, multi-team effort that spans the core of our business including member data, health plan design, provider network information, claims pricing, fraud/waste/abuse detection, billing & payments. We are seeking to automate as close to 100% of our processes as possible, with sub-second latency end-to-end. Challenges include complexity management, compositional architecture, language theory, statistical modeling, etc.


About You:

  • You are passionate about analyzing and helping solve deep technical challenges, and share our fundamental belief that the proper application of technology and 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 in data-intensive engineering organizations.
  • You have deep experience with modern technologies, architectures and agile development methods, and are comfortable (excited by?) operating in complex, fast-moving environments.
  • You have 8+ years of people management experience and can effectively mentor senior leaders on management and technical tracks.
  • You have a track record of building high-functioning teams and can help us attract, develop, and retain the best engineering talent in the industry.
  • You make people and teams around you better through direct yet kind feedback, effective mentorship, and proactive collaboration.
  • You are neither territorial, nor build-an-empire oriented, but rather think, operate and 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 and can help us improve and maintain a great culture where the best ideas prevail, and everyone feels safe and heard.
  • The platform group is approximately 60 engineers and we’re planning to scale to 100+ over the next year. We’re looking for someone who has experienced that scale and growth rate to help us build the team successfully while continuing to enhance our approach to work.



At Oscar, being an Equal Opportunity Employer means more than upholding discrimination-free hiring practices. It means that we work to cultivate an environment where exceptional people can be their most authentic selves and find both belonging and support. We're on a mission to change healthcare -- an experience made whole by your unique background and perspectives.

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 ([email protected]) to make the need for an accommodation known. 

Pay Transparency Policy: Oscar's Pay Transparency Policy 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.


About Oscar

Founded in 2012, Oscar is probably the last thing you would expect from a technology startup – a seemingly old-fashioned healthcare insurance provider. The company provides clients with the kind of clarity and simplicity we have come to expect from an e-commerce site. And, of course, they're hiring.

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