---
title: 'Senior Software Engineer, Cloud Infrastructure / SRE at Oscar Health'
canonical: 'https://feeny.ai/job/senior-software-engineer-cloud-infrastructure-sre-oscar-health-boston-4q2jnnzftygq'
type: 'job'
last_seen: '2026-09-10'
---

# Senior Software Engineer, Cloud Infrastructure / SRE at Oscar Health

- **Company:** Oscar Health
- **Location:** Boston Massachusetts, United States
- **Posted:** 2026-01-28
- **Last confirmed live:** 2026-09-10
- **Apply:** http://www.hioscar.com/careers/7573018?gh_jid=7573018

## Job description

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.

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. Learn more about how you can safeguard yourself from recruitment fraud[here](http://hioscar.com/careers/recruitment-fraud-alert).

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](http://hioscar.com/careers/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 (accommodations@hioscar.com) to make the need for an accommodation known.

California Residents: For information about our collection, use, and disclosure of applicants’ personal information as well as applicants’ rights over their personal information, please see our [Privacy Policy](https://www.hioscar.com/legal/privacy/).

## About Oscar Health

## Company Overview
- **One-liner**: Oscar Health is a healthcare technology company that builds a full-stack health insurance platform to make high-quality, affordable healthcare accessible for individuals, families, and employers.
- **Entity Type**: Public (NYSE: OSCR)
- **Headquarters**: New York City, USA (TriBeCa)
- **Founded**: 2012
- **Founders**: Mario Schlosser (CTO & Co-Founder); additional co-founders are not publicly detailed in the provided sources.

## Core Business
- **Primary industry**: Health insurance / healthcare technology
- **Target customers**: B2C (individuals, families, Medicare beneficiaries) and B2B (employers through Small Group plans and ICHRA)
- **Mission**: “Make a healthier life accessible and affordable for all.”

## Products & Services
- **Oscar Individual & Family Plans** – Health insurance sold on- and off-exchange, featuring $0 virtual urgent care, $3 generic medications, and dedicated Care Teams.
- **Medicare Advantage** – Medicare health plans launched in 2020, available in select states.
- **Oscar for Employers (Small Group / ICHRA)** – Employer-sponsored health benefits, including Individual Coverage Health Reimbursement Arrangements (ICHRA).
- **Oscar Provider Platform** – A technology platform that connects providers with Oscar’s member engagement tools.
- **Oscar App & Care Router** – Digital engagement platform that routes members to appropriate care (virtual or in-person) and enables 24/7 communication with a Care Team.

## Market Standing
- **Valuation/Market Cap**: Not directly provided in the search results; as a public company, market cap is available via SEC filings (e.g., ~$6B as of recent market data, but not confirmed in these sources).
- **Key Metric**: Serves approximately 1.6 million members as of August 2024 (the company also reports a figure of ~3.2 million members, possibly including additional plan types or a different measurement).
- **Notable Investors/Partners**: Not specified in the provided search results; the company went public in 2021 and counts major venture firms among its early investors.
- **Growth Signals**: Active in 20 states; member base grew from 1 million in 2022 to over 1.6 million; launched Medicare Advantage in 2020; has 238 active job postings as of the search date, indicating expansion.

## Competitive Advantages
- **Full-stack technology platform** – Oscar owns the entire insurance stack (claims, care management, provider network), enabling data-driven personalization and member engagement.
- **High member trust and engagement** – 68% of members trust Oscar for care guidance; 44% are digitally engaged; Net Promoter Score of 66; 76% have interacted with digital or Care Team channels.
- **Care Team model** – Every member is assigned a dedicated Care Team that coordinates care, reduces costs, and improves outcomes.
- **Virtual care integration** – $0 virtual urgent care with 97% member satisfaction; virtual primary care in some markets.

## Strategic Focus
- **Geographic expansion** – Entering new states and markets, including Medicare Advantage.
- **AI and technology** – Actively investing in AI to improve care routing, cost savings, and member experience (see “AI @ Oscar” page).
- **Provider platform growth** – Scaling the Oscar Provider Platform to partner with independent providers and health systems.
- **Employer market** – Expanding ICHRA and Small Group offerings to reach more businesses.

## Why Work Here
- **Mission-driven culture** – “Change healthcare for good” with a focus on making insurance simple, transparent, and human. Values include transparency, grit, scientific thinking, and “members above all.”
- **Comprehensive benefits** – Health insurance (obviously), 10+ weeks of parental leave, wellness days, fitness classes, mental health support, 401(k) plan, HSAs, and learning & development programs.
- **Offices** – Headquarters in New York City (TriBeCa), plus offices in Los Angeles (Silicon Beach) and Tempe, Arizona (Health Hub). Remote/hybrid policy not explicitly stated, but many roles appear location-flexible.
- **Growth opportunity** – With 238 open positions and recent member growth, employees can work on challenging problems at scale.
- **Diverse and inclusive environment** – Publishes a diversity report and emphasizes belonging; employees describe culture as collaborative and high-impact.

## Sources
1. [hioscar.com/about](https://www.hioscar.com/about)
2. [hioscar.com/careers](https://www.hioscar.com/careers)
3. [hioscar.com/careers/life](https://www.hioscar.com/careers/life)
4. [linkedin.com/company/oscar-health](https://www.linkedin.com/company/oscar-health)
5. [hioscar.com](https://www.hioscar.com/)

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