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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.

Responsibilities

Become an expert on your team's business and technical domains, including DevOps, site reliability, and cloud best practices.
Lead the planning, execution, and release of complex technical projects across multiple teams outside of Core Technology.
Collaborate 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 manage large or complex technology capabilities within their team's domain or spanning multiple domains.
Facilitate, encourage, and enhance cross-team execution and collaboration, proactively mitigating risks to ensure timely delivery.
Contribute significantly to the objectives of their functional group and organization-wide projects.
Drive the prioritization of the technical roadmap and influence the prioritization of the product roadmap and process enhancements within their team.
Actively identify and reduce failure domains, design and build resilient systems, and strive to minimize the 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 they are responsible for.
Own medium to large features or infrastructure projects from technical design through completion.
Ensure compliance with all applicable laws and regulations.
Perform other duties as assigned.

Requirements

6+ years of professional software engineering experience 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-created quality, and building fault-tolerant, scalable software systems.
Demonstrated expertise in the practical application of CS concepts within their team.
Experience setting and enforcing standards for writing stable, correct, and maintainable code.
Experience mentoring and training junior engineers.
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 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: Understanding of at least one coding language for developing scripts and software.
Education: B.S. in Computer Science, a related technical field, or equivalent high-level industry experience.

Skills

DevOps
Site Reliability
Cloud Best Practices
AWS
GCP
Terraform
Kubernetes
CI/CD
ArgoCD
Prometheus
Grafana
IAM
VPC Peering
Istio
Programming

Location

San Francisco, CA

Work Type

Remote
Full-time

Experience Level

Senior
6+ years of professional software engineering experience

Education Level

B.S. in Computer Science, a related technical field, or equivalent high-level industry experience.

Salary/Compensations

$180,504 - $236,911 per year

Benefits

Medical benefits
Dental benefits
Vision benefits
11 paid holidays
Paid sick time
Paid parental leave
401(k) plan participation
Life insurance
Disability insurance
Paid wellness time and reimbursements
Participation in Oscar's unlimited vacation program
Company equity grants
Annual performance bonuses

About the Company

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.

Equal Opportunity

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.