Senior Software Engineer, Cloud Infrastructure / SRE

Position Summary

Lead technical efforts to build reliable and maintainable applications, infrastructure, and interfaces that make interacting with the health care system easier for members and providers.

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.

Primary Duties and 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 take responsibility for large or complex technology capabilities within your team's domain or spanning multiple domains.
• Facilitate, encourage, and enhance cross-team execution and collaboration; mitigate risk to deliver on time.
• Actively contribute to group and organization-wide objectives.
• Drive prioritization of technical roadmap and influence product roadmap and process enhancements.
• Actively identify and reduce failure domains, design and build resilient systems, and strive to reduce the adverse effects of an outage.
• Build software to minimize effort and business impact during maintenance and failures.
• Guide the development of Service-Level Objectives (SLOs) for systems you are responsible for.
• Own medium to large features or infrastructure projects from technical design through completion.

Required Experience and Education

• 6+ years of professional software engineering experience across a variety of technologies with increasingly impactful accomplishments.
• Experience as a major contributor to cross-pod or cross-company deliverables.
• Experience leading technical contributions, improving quality, and building fault-tolerant, scalable software systems.
• Demonstrated expertise in the practical application of CS concepts.
• Track record of setting and enforcing standards for writing stable, correct, and maintainable code.
• Experience mentoring and training junior engineers.

Bonus Points

• Cloud Proficiency: Deep expertise managing production environments within AWS or GCP at scale.
• Infrastructure as Code: Advanced experience with Terraform or similar IaC tools managing complex multi-account structures.
• Orchestration & Delivery: Proven track record with Kubernetes and workflows using Argo CD.
• SRE Discipline: Strong background in Site Reliability Engineering, including SLOs, error budgets, and incident management.
• CI/CD & Automation: Experience building robust deployment pipelines via GitHub Actions.
• Observability: Proficiency with monitoring tools like Prometheus, Grafana, or similar.
• Security & Networking: Knowledge of cloud-native security (IAM, VPC peering) and service mesh technologies like Istio.
• Programming: Ability to develop scripts and software in at least one coding language.
• Education: B.S. in Computer Science, a related technical field, or equivalent high-level industry experience.