Principal Software Engineer - Full Stack - AI

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 Join our first Dublin engineering team! The International team is seeking a talented and driven Principal Software Development Engineer to join CarGurus' new Dublin office and lead exciting product initiatives for our Canadian and UK markets and play a key role in establishing the office’s culture.  In this role, you’ll be responsible for leading the full software development lifecycle – across both the frontend and backend – collaborating with Engineering and Product peers to design innovative solutions and tackle complex challenges for our dealer-facing products. We are looking for candidates who are able to learn and adapt quickly, and collaborate with other engineers to deliver solutions. Some examples of potential project opportunities: * Building new, full-stack features for dealer products from the ground up * Integrating with existing services and expanding functionality using React, TypeScript, and Java * Designing and implementing integrations with third-party APIs and partners, building applications with Remix. * Modernizing and rearchitecting current systems to leverage cloud technologies like AWS As a principal engineer on this team, you will own projects from conception to completion, working closely with other engineers and product partners, in Dublin and in the US, to deliver impactful solutions for the international business. Success in this role requires a balance of deep technical expertise and strong business judgement to guide teams in making strategic technology decisions that align with both immediate and future product needs. You must quickly learn and adapt to new challenges, working closely with engineers and stakeholders to translate requirements into scalable solutions.  Car expertise is welcome but isn't required; what matters most is your passion for technology, your commitment to engineering excellence, and your drive to have a real impact. What you'll do * Work closely with engineers, product managers, and stakeholders across the company to refine new product requirements and transform them into effective technical solutions. * Own the full development lifecycle from refining initial concepts and architecting advanced features as robust microservices and modern web applications (Java/React/TypeScript), to implementing and delivering practical, high-quality systems. * Contribute to high standards of quality by ensuring code is reliable, performant, and well-tested, with automated tests across the testing pyramid that ensure strong production health of our systems. * Promote a culture of observability and operation excellence by helping teams leverage metrics to diagnose, mitigate, and resolve challenging production issues across multiple services and boost operational excellence. * Use AI technologies, optimizing the software development process and driving greater efficiency across teams. * Mentor engineers by offering guidance, actionable feedback, and insightful recommendations to support sound technical decision-making in the new Dublin hub. What you'll bring * 8+ years of experience as a professional Software Engineer, including 3+ years serving as a technical lead or principal engineer. * Deep full-stack expertise working with Java and TypeScript (or similar languages) and frameworks such as Spring Boot, Hibernate, and React. * 5+ years of experience designing, building, deploying, scaling, testing, and evolving distributed systems using service-oriented architecture in 24/7 production environments. * 2+ years of experience using cloud infrastructure technologies such as AWS, Terraform or similar cloud services. * Hands-on experience working with both relational and NoSQL databases, applying the right data models to diverse needs. * Experience in operating and troubleshooting production systems. * Outstanding written and verbal communication abilities, with a demonstrated talent for translating technical concepts for both engineering and business audiences. * Consistent record of being self-motivated, resourceful, and proactive in driving projects and business goals. * An aptitude for leveraging AI tools such as Claude Code, Cursor, or similar to enhance software development and operational efficiency. Additional hands-on experience with LLMs is a huge plus. * Bonus: Deep experience with server-side TypeScript and modern isomorphic frameworks (especially Remix, though Next.js or Express are also highly valued). 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 €90.000—€108.000 EUR 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

Toast creates technology to help restaurants and local businesses succeed in a digital world, helping business owners operate, increase sales, engage customers, and keep employees happy. Because our technology is purpose-built for restaurants, by restaurant people - and increasingly shaped by AI in both what we build and how we build - restaurants can trust that we'll deliver on their needs for today while investing in the experiences that will power their restaurant of the future. AI Foundations is Toast's internal platform team for AI. We build the infrastructure, governance, and developer tooling that makes AI a reliable, scalable force multiplier across the entire product development lifecycle. Our products include the LLM Proxy, AI Key Management, Observability pipelines, the Claude Plugin Marketplace, and autonomous agents that participate directly in the software development lifecycle. As a Principal Software Engineer, you'll set the technical direction for how we design, build, and evolve these systems, working full-stack across the agentic workflows that employees across Toast depend on every day. This role is for someone who can drive architecture, raise the engineering bar across the team, and stay hands-on building. A day in the life (Responsibilities) * Define and drive the technical architecture for AI Foundations platform, spanning backend services, frontend tooling, and third party integrations * Lead full-stack design and delivery across the LLM proxy, AI key management, observability pipelines, and internal plugin marketplace * Architect and deliver autonomous agents and MCP services that participate in the software development lifecycle * Set and uphold engineering standards across the team: code quality, system design, testing, and operational practices * Mentor and technically lead engineers across all levels through design reviews, code reviews, and pairing * Partner with product and platform leadership to shape the AI Foundations roadmap and translate strategy into executable technical plans * Collaborate closely with designers and product teams to translate UX concepts into polished, production-ready frontend experiences * Serve as a key technical voice in cross-team discussions, representing AI Foundations in architecture decisions across Toast engineering What you'll need to thrive (Requirements) * 10+ years of experience designing and delivering scalable software systems, with a strong full-stack background spanning backend services and frontend or developer-facing interfaces * Demonstrated experience leading technical architecture for a platform, product, or engineering team * Proven ability to mentor engineers and raise the technical bar of a team through standards, reviews, and hands-on guidance * Experience building, deploying, or operating LLM-powered agents or AI platform infrastructure * Familiarity with AI coding assistants (e.g., Claude Code, Cursor, GitHub Copilot) and experience extending them through custom plugins, skills, or hooks * Experience with MCP, tool use patterns, or agentic frameworks * Strong foundation in modern backend (Java, Kotlin, or similar) and frontend (TypeScript, React, or similar) technologies, with demonstrated experience building user-facing product interfaces * Comfort with a rapidly changing technical landscape and a bias towards action over analysis paralysis What will make you stand out * Familiarity with A2A (Agent-to-Agent) protocols and multi-agent orchestration patterns * Experience with machine learning concepts, model evaluation, or ML infrastructure * Experience building developer experience platforms or internal tooling * Familiarity with observability tooling for AI/LLM systems (e.g., Langfuse, DataDog) **This role requires a minimum of two days per week in our Dublin office** AI at Toast At Toast, one of our company values is that we're hungry to build and learn. We believe learning new AI tools empowers us to build for our customers faster, more independently, and with higher quality. We provide these tools across all disciplines, from Engineering and Product to Sales and Support, and are inspired by how our Toasters are already driving real value with them. The people who thrive here are those who embrace changes that let us build more for our customers; it’s a core part of our culture. Our Total Rewards Philosophy  We strive to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and brightest people in our industry. Our total rewards package goes beyond great earnings potential and provides the means to a healthy lifestyle with the flexibility to meet Toasters’ changing needs. Learn more about our benefits at https://careers.toasttab.com/toast-benefits. How Toast Uses AI in its Hiring Process Throughout the hiring process, our goal is to get to know you. We use AI tools to support our recruiters and interviewers with tasks like note-taking, summarization, and documentation of interviews to ensure they can be fully focused on your conversation. All hiring decisions are made by people. To learn more: https://careers.toasttab.com/ai-in-hiring Our Approach to Hybrid Working We embrace a hybrid work model that fosters in-person collaboration while valuing individual needs. Our goal is to build a strong culture of connection as we work together to empower the hospitality community, regardless of location. Please visit the Locations page on our career site to learn more about our in-office expectations by region: https://careers.toasttab.com/locations-toast Diversity, Equity, and Inclusion is Baked into our Recipe for Success At Toast, our employees are our secret ingredient—when they thrive, we thrive. The restaurant industry is one of the most diverse, and we embrace that diversity with authenticity, inclusivity, respect, and humility. By embedding these principles into our culture and design, we create equitable opportunities for all and raise the bar in delivering exceptional experiences. We Thrive Together We embrace a hybrid work model that fosters in-person collaboration while valuing individual needs. Our goal is to build a strong culture of connection as we work together to empower the restaurant community. To learn more about how we work globally and regionally, check out: https://careers.toasttab.com/locations-toast. Apply today! Toast is committed to creating an accessible and inclusive hiring process. As part of this commitment, we strive to provide reasonable accommodations for persons with disabilities to enable them to access the hiring process. If you need an accommodation to access the job application or interview process, please contact candidateaccommodations@toasttab.com. ------ For roles in the United States, it is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.