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Senior Software Engineer, Cloud Infrastructure / SRE

Oscar Health - Remote - Remote - posted 2026-01-28

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Salary: USD 180,504 - 236,911 / annual

Oscar Health is hiring a Senior Software Engineer for Cloud Infrastructure / SRE to join the Core Technology team in Boston. You will work on building and maintaining Oscar's foundational platform, architecting resilient systems using AWS/GCP, Terraform, Kubernetes, and modern CI/CD tooling. The role is fully remote but associated with the Boston metro hub. You will report to a Staff/Senior Staff Engineer and be responsible for becoming an expert in DevOps, site reliability, and cloud best practices. Key responsibilities include leading the planning and execution of complex technical projects across multiple teams, mentoring junior engineers, owning medium-to-large infrastructure projects from design through completion, and actively identifying and reducing failure domains to build resilient systems. You will work with cross-functional partners including product managers and designers to solve challenging problems, drive technical roadmap prioritization, and guide the development of Service-Level Objectives (SLOs) for systems under your purview. The role emphasizes independent ownership of large technical capabilities, facilitating cross-team collaboration, and contributing to organization-wide initiatives. Required qualifications include 6+ years of professional software engineering experience with increasingly impactful accomplishments, demonstrated expertise in leading technical contributions, experience mentoring junior engineers, and a track record as a major contributor to cross-pod or cross-company deliverables. Bonus skills include deep AWS/GCP proficiency, advanced Terraform experience, Kubernetes and ArgoCD expertise, strong SRE discipline with SLOs and incident management, CI/CD pipeline development, observability tools (Prometheus, Grafana), cloud-native security and service mesh technologies, and programming capability in at least one language.

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