Senior Principal Software Engineer, Cloud Architecture

About CarGurus CarGurus was founded in 2006 in Cambridge, Massachusetts by Langley Steinert, co-founder of TripAdvisor, who saw an opportunity to create a better car-shopping experience using technology and data analytics. Today, CarGurus is the leading multinational automotive platform helping consumers and dealers confidently buy and sell vehicles. Our culture fosters kindness, collaboration, and innovation, while empowering Gurus with opportunities and resources to fuel their career growth. We aim to give all people—consumers, dealers, and our employees—the power to reach their destination. Ready to join us for the ride? Apply now!

CarGurus

We give people the power to reach their destination!

C

cargurus.com

1,001-5,000 employees

Technology, Information and Internet

Boston, Massachusetts

2006

Public Company

53k LinkedIn followers

Raised $1.8M

• 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!
• 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.

• 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.
• The displayed range represents the expected annual base salary / On-Target Earnings (OTE) for this position. On-Target Earnings (OTE) is inclusive of base salary and on-target commission earnings, which applies exclusively to sales roles.
• Individual pay within this range is determined by work location and other factors such as job-related skills, experience, and relevant education or training.
• This annual base salary forms part of a comprehensive Total Rewards Package. In addition to benefits, this role may qualify for discretionary bonuses/incentives and Restricted Stock Units (RSUs).
• Position Pay Range
• $191,000—$239,000 USD
• 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

• Equity
• Discretionary bonuses
• Restricted Stock Units
• Career development programs
• Corporate giving programs
• Employee resource groups
• Daily free lunch
• New car discount
• Meditation apps
• Fitness apps
• Commuting cost coverage
• Paid time off