Senior Software Engineer, Cloud Infrastructure / SRE

Position Summary

Oscar is hiring a Senior Software Engineer, Cloud Infrastructure / SRE to join our Engineering team. You will lead technical efforts to build reliable and maintainable applications, infrastructure, and interfaces that make interacting with the healthcare system easier for members and providers.

Our Core Technology teams build and maintain the foundational platform upon which all Oscar engineering is built. We architect a resilient ecosystem using a modern stack centered on AWS/GCP, Terraform, and Kubernetes with developer-focused tooling and CI/CD to provide an automated, self-service infrastructure.

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 the team's domain or spanning multiple domains.
• Facilitate, encourage, and enhance cross-team execution and collaboration; identify risks and actively mitigate them to deliver on time.
• Actively identify and reduce failure domains, design and build resilient systems, and strive to reduce adverse effects of outages.
• 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.

Requirements

• 6+ years of professional software engineering experience, working with a variety of technologies and delivering increasingly impactful accomplishments.
• Experience as a major contributor to cross-pod or cross-company deliverables.
• Experience leading technical contributions, improving team quality, and building fault-tolerant, scalable software systems.
• Demonstrated expertise in the practical application of computer science concepts.
• Demonstrated track record of setting and enforcing standards for 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 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 use at least one coding language to develop scripts and software.
• Education: B.S. in Computer Science, a related technical field, or equivalent high-level industry experience.