Senior Software Engineer, Cloud Infrastructure / SRE oscar · Boston · Site Reliability $180,504-$236,911 8mo ago

Hi, we're Oscar. We're hiring a Senior Software Engineer, Cloud Infrastructure / SRE to join our Engineering team.

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.

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.

You will report into a Staff/Senior Staff Engineer.

Work Location

This is a remote position, open to candidates who reside in: Boston, MA. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area.

Pay Transparency

The base pay for this role is: $180,504 - $236,911 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants, and annual performance bonuses.

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 their team's domain or spanning multiple domains
• Facilitates, encourages, and enhances cross-team execution and collaboration; knows when cross-team projects are at risk and actively mitigates risk to deliver on time
• Prolific contributor to the objectives of their functional group, as well as organization-wide projects
• Drives prioritization of technical roadmap and influences prioritization of product roadmap and process enhancements within their team
• Actively identifies and reduces failure domains, designs and builds resilient systems, and strives to reduce adverse effects of an outage.
• Builds software to minimize effort and business impact during maintenance and failures
• Guides 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
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements

• 6+ years of professional software engineering experience, working with a variety of technologies, and have increasingly impactful accomplishments
• Experience as a major contributor cross-pod or cross-company deliverables
• Experience leading technical contributions, improving the quality of what your teams create, and are excited to build fault-tolerant, and scalable software systems.
• Demonstrates expertise of the practical application of CS concepts within their team.
• Sets and enforces the standard for writing 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 ArgoCD.
• 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 that you are able to use to develop scripts and software
• Education: B.S. in Computer Science, a related technical field, or equivalent high-level industry experience.

This is an authentic Oscar Health job 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.

Pay Transparency

Final offer amounts, within the base pay set forth above, are determined by factors including your relevant skills, education, and experience. Full-time employees are eligible for benefits including: medical, dental, and vision benefits, 11 paid holidays, paid sick time, paid parental leave, 401(k) plan participation, life and disability insurance, and paid wellness time and reimbursements.

Artificial Intelligence (AI)

Our AI Guidelines outline the acceptable use of artificial intelligence for candidates and detail how we use AI to support our recruiting efforts.

Reasonable Accommodation

Oscar applicants are considered solely based on their qualifications, without regard to applicant's disability or need for accommodation. Any Oscar applicant who requires reasonable accommodations during the application process should contact the Oscar Benefits Team (View email address on click.appcast.io) to make the need for an accommodation known.

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