--- title: 'Senior Principal Software Engineer, Cloud Architecture at CarGurus' canonical: 'https://feeny.ai/job/senior-principal-software-engineer-cloud-architecture-cargurus-boston-m6qnn3vbyaxe' type: 'job' last_seen: '2026-10-30' --- # Senior Principal Software Engineer, Cloud Architecture at CarGurus - **Company:** CarGurus - **Location:** Boston, MA - **Compensation:** $191k–$239k - **Posted:** 2026-10-20 - **Last confirmed live:** 2026-10-30 - **Apply:** https://careers.cargurus.com/us/en/job/8285501?gh_jid=8285501 ## Job description ## 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. ## What you'll do - 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. 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 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 ## About CarGurus ## Company Overview - **One-liner**: CarGurus is the #1 most-visited digital auto platform in the United States, using data-driven technology to bring trust and transparency to car shopping and selling. - **Entity Type**: Public (NASDAQ: CARG) - **Headquarters**: Boston, Massachusetts, USA - **Founded**: 2006 - **Founders**: Langley Steinert (co-founder of TripAdvisor) ## Core Business - **Primary industry**: Automotive marketplace / Digital auto platform - **Target customers**: B2C (car buyers and sellers) and B2B (car dealers) - **Mission statement**: "To give people the power to reach their destination" — empowering drivers and dealers with the confidence to buy or sell cars exactly how they want, whether online, in-person, or a combination of both. ## Products & Services - **CarGurus Marketplace (Consumer)**: A data-driven car shopping platform featuring over 4 million vehicle listings in the US. The platform provides unbiased vehicle information, Instant Market Value (IMV) pricing, deal ratings (Great/Good/Overpriced), and a "Best Match" sort order to help consumers find the best deal. Includes tools for buying, financing, and selling. - **CarGurus for Dealers (B2B)**: A suite of digital retail tools and services that help tens of thousands of dealers source, market, and sell vehicles. Includes digital retailing tools for financing, appointment booking, and online sales. - **Autolist**: A car shopping platform acquired by CarGurus in 2020, expanding the consumer audience. - **PistonHeads**: A UK-based motoring community and automotive marketplace acquired in 2019. ## Market Standing - **Valuation/Market Cap**: Publicly traded on NASDAQ under ticker CARG. Market cap fluctuates; as of mid-2025, it is approximately $3.5–4 billion (check latest). - **Key Metric**: $907 million in revenue in FY2025. - **Notable Investors/Partners**: Public company with institutional investors; founded by Langley Steinert (co-founder of TripAdvisor). - **Growth Signals**: - #1 most-visited automotive platform in the US with 45 million monthly visitors and 39.7 million monthly unique visitors. - Over 4 million vehicle listings in the US. - Serves 24,000+ US dealers and 34,000 dealers globally. - 1,100+ employees across North America, Ireland, and the UK. - Launched an AI-powered shopping experience in 2025. - Expanded digital retail tools (financing, appointment booking) in 2022. - Acquired Autolist (2020) and PistonHeads (2019) to expand audience and geographic reach. ## Competitive Advantages - **Data-driven transparency**: Proprietary Instant Market Value (IMV) and deal ratings (Great/Good/Overpriced) provide unbiased pricing insights that build consumer trust. - **Scale and audience**: #1 most-visited automotive platform in the US with 45M monthly visitors, giving it unmatched reach for both consumers and dealers. - **Dual-sided marketplace**: Serves both consumers (B2C) and dealers (B2B), creating a powerful network effect — more buyers attract more dealers, and more listings attract more buyers. - **Technology-first approach**: A tech company at its core, leveraging data science, AI, and rapid iteration to improve the car buying/selling experience. - **Brand trust and transparency**: Long-standing reputation for unbiased data (Instant Market Value, deal ratings) that differentiates it from traditional classifieds. ## Strategic Focus - **AI and personalization**: Launching an AI-powered shopping experience (2025) to create a more personalized and intuitive research process. - **Digital retail expansion**: Continuing to build out digital retail tools (financing, appointment booking) to enable more of the car sale to happen online. - **Dealer partnership growth**: Deepening relationships with the 34,000+ dealers who use the platform to maximize their revenue. - **International presence**: Maintaining and growing operations in the US, Canada, UK, and Ireland. ## Why Work Here - **Culture and values**: CarGurus emphasizes integrity, transparency, data-driven decision-making, speed, collaboration, and pioneering spirit. The company is Built In’s #1 Best Large Company to Work For in the U.S. and #1 Best Place to Work in Boston. - **Work model**: Flexible hybrid model with a headquarters in Boston's Back Bay. The office features open seating, innovation areas, a 24/7 fitness center, rooftop terraces, fully stocked kitchens, and a barista bar. - **Time off**: Full-time US employees get unlimited personal and sick time off, plus 3 weeks of vacation to start. Dublin and UK employees get 25 days annual leave and 10 sick days. All employees receive a month-long paid sabbatical after 5 and 10 years. - **Perks**: $15/day in-office lunch stipend, commuting and tuition support, gym/wellness reimbursement, meditation and fitness app subscriptions, and an "Auto Perk" of up to $1,250 toward a new vehicle purchase from a dealer partner. - **Family support**: Partnerships with Carrot Fertility and Care.com (for daycare, eldercare, and pet care), plus family-focused leave policies. - **DEIB**: No dress code, employee-led charitable giving, donation matching, and a focus on diversity, equity, inclusion, and belonging. - **Learning**: Tailored development programs, on-demand content, annual Hackathon and Science Fair. - **Culture**: Emphasizes integrity, transparency, collaboration, speed, and a pioneering spirit. "Being a car person is optional" — the company values curiosity and problem-solving over automotive passion. ## Sources 1. [cargurus.com](https://www.cargurus.com/about/cargurus) 2. [careers.cargurus.com](https://careers.cargurus.com/us/en/) 3. [careers.cargurus.com (Life page)](https://careers.cargurus.com/us/en/life) 4. 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