Senior DevOps Engineer

CarGurus • Boston, MA

8d • Hybrid

About The Position

At CarGurus (NASDAQ: CARG), our mission is to give people the power to reach their destination. We started as a small team of developers determined to bring trust and transparency to car shopping. Since then, our history of innovation and go-to-market acceleration has driven industry-leading growth. In fact, we’re the largest and fastest-growing automotive marketplace, and we’ve been profitable for over 15 years.
What we do
The market is evolving, and we are too, moving the entire automotive journey online and guiding our customers through every step. That includes everything from the sale of an old car to the financing, purchase, and delivery of a new one. Today, tens of millions of consumers visit CarGurus.com each month, and ~30,000 dealerships use our products. But they're not the only ones who love CarGurus—our employees do, too. We have a people-first culture that fosters kindness, collaboration, and innovation, and empowers our Gurus with tools to fuel their career growth. Disrupting a trillion-dollar industry requires fresh and diverse perspectives. Come join us for the ride!
CarGurus is seeking a Senior DevOps Engineer to join our Cloud Infrastructure team. This team is responsible for providing a reliable, secure, and consumable AWS based platform for revenue-generating applications and the product engineering teams behind them.
In this role you will be a key owner of the cloud platforms that power our global automotive marketplace, and you will help build opinionated, self-service infrastructure that lets engineers ship fast, safely, and with confidence. We are looking for a resourceful, curious individual who is energized by the prospect of designing thoughtful, scalable platforms that are essential to engineers across the entire company.
Role overview
Our team is responsible for designing and operating the core cloud infrastructure at CarGurus. This includes managing domains such as governance, cost attribution, networking, serverless workloads, and OS configuration/orchestration. We also handle CarGurus' edge infrastructure (registrars, DNS, CDN) and maintain essential shared engineering systems like GitHub, Artifactory, and Rundeck, which are critical for how our engineers build, deploy, and operate services.

Requirements

• Cloud Infrastructure & Operations: Deep experience operating production workloads in public/private cloud environments, utilizing role-based security, APIs, and production telemetry (metrics, logs, alerts) to enhance reliability and performance.
• Infrastructure as Code & CI/CD: Extensive background with infrastructure as code, configuration management, and CI/CD pipelines such as Terraform, Chef, Ansible, Puppet, GitHub Actions, or similar.
• Linux/Unix & Programming: Strong, hands-on Linux/Unix experience and proficiency in at least one high-level programming language such as Python, Ruby, Go or similar.
• Container/Orchestration: Experience with container or VM orchestration platforms such as Kubernetes/Helm/EKS, OpenShift, VMware, or similar.
• Networking & Security: Solid understanding of IP network routing, DNS, load balancing, security, and edge/CDN concepts.
• Web Application Familiarity: Familiarity with large-scale Java web application development and production operations, or similar high-volume environments.
• Ownership & Communication: Proven ability to manage projects and communicate clearly and effectively with stakeholders.
• Partnership with Stakeholders: Proactive approach to partnering with cross-functional stakeholders to align infrastructure strategy with business goals and drive shared outcomes.
• Problem-Solving: Self-starter mindset with strong curiosity and a hands-on bias for problem-solving. Willingness to take calculated risks to deliver elegant solutions.
• Decision Making: Comfortable navigating ambiguity to uncover root drivers and making practical, well-reasoned design decisions.

Responsibilities

• Platform Development & Evolution: Design, build, and operate CarGurus' production infrastructure in collaboration with support and build/delivery platform teams. Evolve compute, storage, and data platforms on AWS (e.g., S3, EC2, EKS, ELB, Route53, IAM).
• Automation & Infrastructure-as-Code (IaC): Drive IaC and automation practices (Terraform, Chef, Git, GitHub Actions, Concourse) to ensure secure, repeatable lifecycle operations.
• Cloud Governance: Shape and implement cloud governance, tagging, and reporting standards to support resource attribution and ownership.
• Networking & Edge Operations: Design and operate cloud networking, data protection mechanisms, and edge access components (Fastly CDN, Route53, HAProxy, Datadome).
• Self-Service & Developer Workflow: Utilize, support and enhance self-service platform offerings using AWS, AI and IaC patterns via Terraform.
• Shared Tools Ownership: Own and improve shared production tools and platforms such as Rundeck, GitHub, and Artifactory.
• Incident Management: Participate in incident response and on-call rotation.
• Mentorship & Documentation: Create and maintain documentation to facilitate the adoption and operation of platform services.
• Innovation: Utilize AI-assisted design and internal tools to explore new architectures, validate trade-offs, and accelerate the design and evolution of platform services and infrastructure.
• Agile Practices: Participate in the team's agile workflow and ceremonies.

Benefits

• We reward our Gurus’ curiosity and passion with best-in-class benefits and compensation, including equity for all employees, both when they start and as they continue to grow with us.
• Our career development and corporate giving programs, as well as our employee resource groups (ERGs) and communities, help people build connections while making an impact in personally meaningful ways.
• A flexible hybrid model and robust time off policies encourage work-life balance and individual well-being.
• Thoughtful perks like daily free lunch, a new car discount, meditation and fitness apps, commuting cost coverage, and more help our people create space for what matters most in their personal and professional lives.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed
• Number of Employees: 501-1,000 employees