Hi, we're Oscar. We're hiring a Senior Software Engineer, Cloud Infrastructure / SRE to join our Engineering team.
Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.
About the role:
Our Core Technology teams build and maintain the foundational platform upon which all Oscar engineering is built. We are responsible for architecting a world-class, resilient ecosystem using a modern stack centered on AWS/GCP, Terraform, and Kubernetes with developer focused tooling and CI/CD. Our mission is to provide an automated, self-service infrastructure that empowers our engineering organization to move fast without sacrificing security or stability.
You will report into a Staff/Senior Staff Engineer.
Work Location: This is a remote position, open to candidates who reside in: San Francisco, CA. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area. #LI-Remote
Pay Transparency: The base pay for this role is: $180,504 - $236,911 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants, and annual performance bonuses.
Responsibilities:
- Become the expert on your team's business and technical domains such as DevOps, site reliability, and cloud best practices
- Lead the planning, execution and release of complex technical projects across multiple teams outside of Core Technology
- Work with partners, product managers, and designers to solve challenging problems
- Lead and mentor engineers on the team to improve technology and apply best practices
- Independently responsible for large or complex technology capabilities (set of components or services) within their team's domain or spanning multiple domains
- Facilitates, encourages, and enhances cross-team execution and collaboration; knows when cross-team projects are at risk and actively mitigates risk to deliver on time
- Prolific contributor to the objectives of their functional group, as well as organization-wide projects
- Drives prioritization of technical roadmap and influences prioritization of product roadmap and process enhancements within their team
- Actively identifies and reduces failure domains, designs and builds resilient systems, and strives to reduce adverse effects of an outage.
- Builds software to minimize effort and business impact during maintenance and failures
- Guides the development of Service-Level Objectives (SLOs) for systems they are responsible for
- Own medium to large features or infrastructure projects from technical design through completion
- Compliance with all applicable laws and regulations
- Other duties as assigned
Requirements:
- 6+ years of professional software engineering experience, working with a variety of technologies, and have increasingly impactful accomplishments
- Experience as a major contributor cross-pod or cross-company deliverables
- Experience leading technical contributions, improving the quality of what your teams create, and are excited to build fault-tolerant, and scalable software systems.
- Demonstrates expertise of the practical application of CS concepts within their team.
- Sets and enforces the standard for writing stable, correct, and maintainable code
- Experience mentoring and training more junior engineers
Bonus points:
- Cloud Proficiency: Deep expertise in managing production environments within AWS or GCP at scale.
- Infrastructure as Code: Advanced experience with Terraform or similar IaC tools to manage complex, multi-account structures.
- Orchestration & Delivery: Proven track record with Kubernetes and workflows using ArgoCD.
- SRE Discipline: Strong background in Site Reliability Engineering, including Service Level Objectives (SLOs), error budgets, and incident management.
- CI/CD & Automation: Experience building robust deployment pipelines via GitHub Actions.
- Observability: Proficiency with monitoring using tools like Prometheus, Grafana, or similar.
- Security & Networking: Knowledge of cloud-native security (IAM, VPC peering) and service mesh technologies like Istio.
- Programming: Understanding of at least one coding language that you are able to use to develop scripts and software
- Education: B.S. in Computer Science, a related technical field, or equivalent high-level industry experience.
This is an authentic Oscar Health job opportunity. Learn more about how you can safeguard yourself from recruitment fraud here.
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.
Pay Transparency: Final offer amounts, within the base pay set forth above, are determined by factors including your relevant skills, education, and experience. Full-time employees are eligible for benefits including: medical, dental, and vision benefits, 11 paid holidays, paid sick time, paid parental leave, 401(k) plan participation, life and disability insurance, and paid wellness time and reimbursements.
Artificial Intelligence (AI): Our AI Guidelines outline the acceptable use of artificial intelligence for candidates and detail how we use AI to support our recruiting efforts.
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 ([email protected]) to make the need for an accommodation known.
California Residents: For information about our collection, use, and disclosure of applicants’ personal information as well as applicants’ rights over their personal information, please see our Privacy Policy.
Skills Required
- 6+ years of professional software engineering experience
- Major contributor to cross-pod or cross-company deliverables
- Experience leading technical contributions and building fault-tolerant, scalable software systems
- Demonstrated practical expertise applying computer science concepts
- Sets and enforces standards for writing stable, correct, and maintainable code
- Experience mentoring and training more junior engineers
- Deep expertise managing production environments in AWS or GCP at scale
- Advanced experience with Terraform or similar Infrastructure as Code tools
- Proven track record with Kubernetes and ArgoCD
- SRE experience including SLOs, error budgets, and incident management
- Experience building CI/CD pipelines via GitHub Actions
- Proficiency with observability tools such as Prometheus and Grafana
- Knowledge of cloud-native security (IAM, VPC peering) and service mesh technologies (Istio)
- Understanding of at least one programming language for scripting and software development
- B.S. in Computer Science or related field, or equivalent experience
Oscar Health Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Oscar Health and has not been reviewed or approved by Oscar Health.
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Healthcare Strength — Employer-sponsored medical coverage for employees and their families with mental-health support is prominently offered. Wellness programming and digital care access add to perceived strength.
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Parental & Family Support — Paid parental leave of 10+ weeks, backup care, and family-forming support (including fertility and adoption benefits) are part of the package. Reproductive‑loss leave is also noted.
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Leave & Time Off Breadth — Multiple time‑off options, wellness days, and an unlimited vacation program for some roles are described. Paid holidays, paid sick time, and a long‑tenure sabbatical broaden time‑away choices.
Oscar Health Insights
What We Do
Health care is broken; we're trying to fix it. The Oscar team is focused on utilizing technology, design and data to humanize health care. We're a group of technology and health care professionals who looked at the current state of the US health care system, got frustrated by the horrible consumer experience, and decided to do something big about it. Backed by a renowned set of investors and advisors, we’ve set out to revolutionize health care.
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