Senior Software Engineer, Cloud Infrastructure / SRE

Oscar Health•Boston, MA

5h•Remote

About The Position

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. #LI-Remote 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.

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

Nice To Haves

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.

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