Investing in the Future
of Insurance

Senior DevOps Engineer

Polly

Polly

Software Engineering
Vermont, USA · Remote
Posted on Oct 16, 2025
Senior DevOps Engineer

Job Overview

Sr. DevOps Engineer

THE ROLE

The Senior DevOps Engineer takes the lead in shaping our cloud platform and developer enablement strategy. In this high-impact role, you’ll have broad authority and autonomy to define the architecture, tools, and practices that power our cloud-hosted systems. You’ll design and build modern, scalable infrastructure; establish best practices for CI/CD, observability, and security; and create the tooling that helps our developers move fast with confidence. This is a rare opportunity for a hands-on technical leader who wants to set direction, drive innovation, and make a lasting mark on how software is built and delivered.

WHAT YOU'll DO

  • Design, implement, and maintain Infrastructure as Code (IaC) to automate provisioning, configuration, and scaling of cloud environments using tools such as Terraform, Pulumi, or Bicep.
  • Own the CI/CD strategy and toolchain, designing pipelines that enable rapid, reliable, and secure delivery of applications and infrastructure changes.
  • Establish and enforce DevOps best practices for version control, testing, deployment, and rollback across multiple environments.
  • Build and maintain reusable infrastructure modules and templates to support consistent, secure, and efficient deployments.
  • Collaborate with development teams to integrate CI/CD pipelines with application codebases, test suites, and runtime configurations.
  • Monitor, optimize, and troubleshoot pipeline performance and reliability, ensuring fast feedback loops and minimal downtime.
  • Implement observability, logging, and alerting frameworks to improve visibility into infrastructure health and deployment outcomes.
  • Champion automation and self-service, reducing manual processes and empowering developers with scalable, reliable tools.
  • Evaluate and introduce new technologies and practices to improve the security, resilience, and developer experience of the platform.
  • Provide mentorship and technical leadership, helping engineers adopt infrastructure-as-code and CI/CD practices effectively.

WHAT YOU'LL NEED TO SUCCEED

Required

  • 5+ years of experience in DevOps, Cloud Engineering, or related software infrastructure roles.
  • Proven expertise in designing and implementing Infrastructure as Code (IaC) using tools such as Terraform, Pulumi, or Bicep.
  • Strong background in CI/CD pipeline development and automation, using systems such as GitHub Actions, Azure DevOps Pipelines, Jenkins, or similar.
  • Deep understanding of cloud-native architectures, containerization (Docker/Kubernetes), and modern deployment strategies (e.g., blue/green, canary).
  • Solid grasp of networking, identity, and security principles in cloud environments.
  • Experience with monitoring, observability, and incident response practices and tooling.

Preferred

  • Hands-on experience with Microsoft Azure as the primary cloud platform.
  • Familiarity with Azure Container Apps, Azure Key Vault, and related services.
  • Strong understanding of GitHub Enterprise integrations for source control and automation.
  • Experience designing multi-environment and multi-tenant architectures in Azure.
  • Knowledge of policy-as-code and security-as-code implementations within Azure ecosystems.
  • Prior experience leading DevOps strategy or setting organizational infrastructure standards.

Education

  • Bachelor’s degree in Computer Science or related degree preferred or 10+ years of cumulative DevOps experience

WORK AND LIFE BALANCED, WE’RE HERE FOR YOU

  • Medical, dental and vision insurance
  • HSA, FSA, Dependent Care FSA and Commuter pre-tax benefit
  • Flextime PTO and generous holiday time
  • Paid Parental leave + baby cash
  • Matching 401(k) contributions
  • Life & disability Insurance
  • Work from anywhere options

About Polly
Polly delivers unexpected value by embedding insurance into life's biggest purchases. As the leading embedded automotive insurance marketplace, Polly seamlessly integrates coverage options from 40+ insurance carriers into the automotive buying experience at thousands of dealerships across the country, delivering savings to consumers when they need it most. With more than $11 billion in coverage placed, shoppers trust Polly for instant quotes, immediate coverage, and expert live agents. Experience the unexpected value of embedded auto insurance at Polly.co.

Polly is an equal opportunity employer, and all qualified applicants will receive consideration for employment without regard to race, color, religion, gender, national origin, age, genetic information, creed, marital status, sexual orientation, gender identity, disability status, protected veteran status, or any other protected status as defined by federal, state or local law.