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. 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 to a Staff/Senior Staff Engineer. This position requires a hybrid work schedule in our New York City office (3 days per week, with Thursdays required for team meetings and events).

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 team domains or spanning multiple domains
• Facilitate, encourage, and enhance cross-team execution and collaboration; actively mitigate risk to deliver on time
• Serve as a prolific contributor to the objectives of the functional group and organization-wide projects
• 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 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
• Ensure compliance with all applicable laws and regulations

Requirements

• 6+ years of professional software engineering experience working with a variety of technologies and 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 CS concepts within the team
• 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 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 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 used to develop scripts and software
• Education: B.S. in Computer Science, a related technical field, or equivalent high-level industry experience