Principal Software Engineer Visa Sponsorship Jobs in Massachusetts

Who we are

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!

Role overview

CarGurus is hiring a Senior Principal Software Engineer to be the hands-on cloud architect within our Engineering Platform (EP) organization. We have finished a large lift-and-shift to AWS. The next step is helping 300+ engineers build cloud-native, SaaS-ready software that is resilient, secure, and built to scale. In this role you will work hands-on, side by side with the teams doing the work. You won't belong to a single squad. Instead, you will go wherever the hardest system and cloud architecture problems are, partner with teams to solve them, and leave behind patterns that others can reuse.

• Own system architecture as it connects to cloud architecture: shape how services, data, and jobs map onto AWS, and lay out practical paths from old architectures to new ones.
• Partner with Product Engineering teams on their architecture problems. This may mean working closely with a team for a period of time to prototype, help unblock them, and leave behind an architecture they can own.
• Act as the technical lead for our AWS relationship. You'll work with AWS solutions architects on service guidance and roadmaps.
• Build proofs of concept and reference implementations in code, using Terraform, Python, Java, and similar tools, that teams can build on and that can evolve into standard patterns over time. Explain the trade-offs behind each one.
• Work with Cloud Enablement to advance AWS self-service and guardrails: HCP Terraform workflows, Sentinel policies, IAM, and account and sandbox strategy.
• Design architecture with cost in mind across cloud and AI spend, including attribution, tagging, and controls.
• Lead architecture for SaaS maturity and compliance readiness, covering disaster recovery and business continuity, security, performance, dependency ownership, and standardizing our cloud accounts.
• Guide architecture for agentic workloads on AWS, such as AgentCore Gateway, Bedrock, OAuth, and machine-to-machine identity, in partnership with InfoSec.
• Collaborate with our Technical Leadership Team to shape technical direction. Record decisions in ADRs and RFCs and spread them across teams.
• Mentor senior engineers and run workshops on cloud-native best practices.

What you'll bring

• 10+ years of software engineering experience, including 5+ years designing and running production systems on AWS.
• A software engineer first: you write production-quality code in at least one of Java, Python, TypeScript, or Go.
• Fluent in infrastructure as code with Terraform.
• Deep AWS expertise across networking (VPC, Transit Gateway, VPC Lattice), IAM, serverless (Lambda, Batch, API Gateway), containers (EKS), and managed data stores.
• Focused on security: least-privilege IAM, OAuth2/OIDC, and designing for compliance.
• Bring a forward-deployed mindset: you would rather build the prototype than only review the design, and you can still write the think paper that sets direction.
• Lead through influence and collaboration without ego. You build trust with engineers, managers, and executives, both inside and outside your own organization.
• Write clearly and can explain technical trade-offs to technical and non-technical audiences.
• Think about cost: you treat cost efficiency as a design requirement.

Working at CarGurus

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.

CarGurus may require in-person interviews as part of our hiring process, particularly for positions based in our Boston and Dublin offices. Candidates selected for an in-person interview will be notified in advance. Please be aware that travel expenses are the responsibility of the candidate.

We welcome all

CarGurus strives to be a place to which people can bring the ultimate expression of themselves and their potential—starting with our hiring process. We do not discriminate based on race, color, religion, national origin, age, sex, marital status, ancestry, physical or mental disability, veteran status, gender identity, or sexual orientation. We foster an inclusive environment that values people for their skills, experiences, and unique perspectives. That's why we hope you'll apply even if you don't check every box listed in the job description. We also encourage you to tell your recruiter if you require accommodations to participate in our hiring process due to a disability so we can provide the appropriate support. We want to know what only you can bring to CarGurus. #LI-Hybrid