
Cargurus · Boston
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 ...
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 transforming how the company operates by embedding AI into workflows across every function — product, engineering,
revenue, finance, support. It’s a software engineering role where the domain is the entire business. You’ll work directly with
teams across the org to understand how work actually gets done, identify where AI can change the unit of work or shift where
judgment lives, and build the systems that make it real. Some of that is agent-based automation. Some of it is workflow redesign.
All of it requires someone who can architect and ship production-quality software, not stitch together SaaS integrations. This is
not a Salesforce developer, Boomi connector, or low-code/no-code position, nor is it an enterprise architect or ML model training
role.
This is a small, high-autonomy team reporting to the Head of AI Solutions. You’ll have outsized influence on how a publicly traded
company with ~$1B in revenue adopts AI — not as a pilot or a demo, but as a structural change in how the business runs. You will
be successful here if you are a product-caliber engineer who finds internal workflow transformation genuinely interesting — not a
consolation prize, but the most leveraged place to be right now. You’d rather build something real that 200 people use tomorrow
than something polished that ships in 6 months.
existing workflows, and identify high-leverage opportunities for AI.
specs.
intelligent tooling.
everything to be clean before you start building.
something that ran in production or was used by real people.
the high-impact problems live.
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
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
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 The Principal IT Systems Administrator is the most senior individual contributor on the IT Systems team, setting technical direction for core platforms, endpoints, networks, and security within IT Operations. This role drives reliability, scalability, and automation. You will lead complex initiatives, serve as a top escalation point, and partner across the business to ensure infrastructure and endpoints enable productivity while meeting security and compliance needs. What you'll do * System Configuration & Administration: Design and implement complex configurations for core IT platforms (identity, collaboration, infrastructure, SaaS). Establish configuration management, lead performance/reliability improvements, and automate repetitive tasks. * Workspace & Endpoint Management: Design enterprise-wide endpoint strategies (macOS, Windows, mobile). Develop and enforce security policies, automate software/OS deployments via MDM/EMM, and own compliance reporting. * Network & Infrastructure: Design and implement complex network configurations (LAN/WAN/Wi-Fi/VPN/voice) for scalability and security. Maintain monitoring, automate network management, and lead infrastructure projects (e.g., migrations, new site buildouts). * Security Engineering & Operations: Define and drive security strategies within IT Systems (identity, access, endpoints, networks). Integrate security tools (SSO/MFA, EDR, DLP), enforce access policies, and act as a technical lead during critical security incidents. * Incident Management & Reliability: Define and implement incident response strategies, lead Post-Incident Reviews (PIRs) to drive corrective action, develop runbooks, and oversee on-call rotations. * Documentation & Knowledge Management: Define documentation standards (architecture, SOPs, runbooks) and ensure knowledge bases are accurate, comprehensive, and easily discoverable. What you'll bring * Extensive experience (typically 8+ years) in IT systems engineering/administration, with significant time in senior/lead roles on enterprise-scale environments. * Deep expertise in: Core IT systems (identity, collaboration, directory), Endpoint management (MDM/EMM, lifecycle), Network infrastructure (switching, routing, VPN), and Security controls (EDR, SSO/MFA). * Demonstrated ability to design complex configurations, lead large cross-functional projects, and influence architectural decisions. * Strong automation mindset and proficiency with scripting/infrastructure-as-code (Python, PowerShell, Terraform). * Proven track record leading major incidents and PIRs. * Excellent cross-functional collaboration and communication skills, comfortable engaging all levels. * Experience in environments with security, regulatory, or audit requirements (SOC 2, SOX). * A bias toward ownership, documentation, and mentorship. Nice to have: Experience in a high-growth SaaS or technology company, familiarity with CarGurus tools (Okta, Google Workspace/M365, Jamf, Intune), and experience partnering with Security Engineering and GRC. 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 $113,000—$142,000 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
We fuse together exceptional talent who deliver outstanding software solutions. Our approach has helped us grow 60% in 2021, 94% in 2022, while in 2023 we joined forces with Insight, a Fortune 500 company and a leading solutions and systems integrator. With exciting growth plans and cutting-edge projects, there has never been a better time to join our incredible team. ABOUT THE JOB We fuse together exceptional talent who deliver outstanding software solutions. Our approach has helped us grow 60% in 2021, 94% in 2022, while in 2023 we joined forces with Insight, a Fortune 500 company and a leading solutions and systems integrator. With exciting growth plans and cutting-edge projects, there has never been a better time to join our incredible team. We are establishing a AI Engineering team who will work closely with our most strategic customers to deeply understand their use cases and design, build, and implement products for them. As one of our founding AIs, you will deploy these solutions on the latest infrastructure for the world's most influential businesses, driving real business impact through the newest models and our own innovations in technical delivery. AI Engineers' responsibilities look similar to those of a hands-on AI startup CTO: you'll work in small teams to own delivery of high stakes projects with clients. A day's work may include building LLM workflows on a large scale, interacting with customers to understand their needs and set their AI strategy, but the most impact will be driven by implementing solutions into the real world of our partner's organizations. We are looking for customer-focused software engineers to build effective custom software that leverages leading AI models and technology to solve real customer problems. You will partner directly with customers to conceptualize, design, and implement cutting-edge AI solutions. This role focuses on leveraging generative AI models, agentic systems, and iterative prototyping to build impactful proofs of concept (PoCs) that address unique business challenges. The AI engineer acts as a bridge between advanced AI technologies and practical enterprise applications, ensuring that solutions are both innovative and actionable. You will collaborate closely with Sales, Solutions Engineering, Solutions Architects, and Customer Success Managers who work on the same account. You will also be self driven to learn about the AI market and bring forward that knowledge to improve the way in which we deliver to customers. Responsibilities Customer Engagement: Collaborate deeply with clients to understand their strategic objectives, technical requirements, and operational constraints. Serve as a trusted advisor for AI strategy, guiding clients through the process of ideating and implementing generative and agentic AI solutions. Facilitate workshops and brainstorming sessions to identify high-value use cases for AI technologies. AI Solution Development: Design, prototype, and deploy AI-powered PoCs using generative models (e.g., GPT, DALL-E) and agentic systems tailored to specific client needs. Build end-to-end pipelines for deploying AI solutions on client infrastructure, ensuring scalability, security, and performance. Experiment with cutting-edge methods in natural language processing (NLP), computer vision, reinforcement learning, and multi-agent systems to deliver innovative solutions. Iterative Prototyping: Use an experiment-driven approach to rapidly test hypotheses and refine prototypes in collaboration with client teams. Develop reusable frameworks and tools to accelerate the deployment of generative AI solutions across diverse industries. Cross-Functional Collaboration: Work closely with Sales, Applied Research, Product Development, and Customer Success teams to ensure seamless project execution. Provide actionable feedback from customer engagements to inform the development of new AI capabilities. Knowledge Sharing: Document best practices and lessons learned from client projects to contribute to internal knowledge bases. Mentor junior engineers on the application of generative and agentic AI technologies in real-world scenarios. Requirements Technical Expertise: Strong proficiency in programming languages such as Python or JavaScript, with experience in frameworks like TensorFlow or PyTorch. Hands-on experience with generative AI models (e.g., GPT-4/5), agentic systems, or reinforcement learning frameworks. Familiarity with deploying machine learning models in production environments using cloud platforms (e.g., AWS, Azure) or on-premise systems. Problem-Solving Ability: Proven ability to translate abstract business challenges into concrete technical solutions using generative AI. Strong analytical skills to evaluate model performance and optimize for specific use cases. Client-Facing Skills: Exceptional communication skills for explaining complex AI concepts to diverse stakeholders. Ability to build trust-based relationships with clients and navigate ambiguous problem domains collaboratively. Adaptability: Flexibility to work across industries such as healthcare, finance, defense, or retail while tailoring solutions to each domain. Willingness to travel or work on-site with clients as required. Requirements (Education, Certification, Training, and Experience) Bachelor's degree in computer science or related field or equivalent experience At least 3 years of experience in software engineering or applied machine learning roles. Direct experience working with customers on the development of AI-driven applications is highly desirable Passion for exploring the frontiers of generative and agentic AI technologies. Entrepreneurial mindset with a focus on delivering measurable business impact through innovative solutions. Commitment to continuous learning and staying at the forefront of AI advancements. This role is ideal for those who thrive at the intersection of technology innovation and customer engagement. You will have the opportunity to shape the future of enterprise AI adoption while solving some of the most complex challenges faced by leading organizations. BENEFITS * Opportunities for certification and training * Dual monitor setup and high-spec workstations * English courses * Gym allowance * Medical Reimbursement * Full salary covered up to 20 days of sickness * Flexible working hours * Loyalty scheme * Team building activities, special events and conferences * UK/EU Travel opportunities * Snacks and drinks in the office To see more roles, click here.
ÜBER UNS The appliedAI Initiative elevates Europe’s industry to become shapers in the age of AI, creating a future that we desire to live in. Through our ecosystem of strong partners, comprehensive programs, services and solutions we advance companies holistically on their AI journey. With our uniquely diverse, interdisciplinary, and driven team, we build on deep technical expertise while specializing on applicability of the solutions. We share a mindset of collaboration and openness with our ecosystem of leading companies and tech players. Our common goal is to strengthen the European landscape, jointly creating unique knowledge for applying trustworthy AI. We believe that AI Agents will be the dominant topic for AI in the near future and that appliedAI with its partner ecosystem will impact how this technology is being used in industry and beyond in Europe. DEINE AUFGABEN You build the systems other engineers learn from. At appliedAI, we help Europe’s leading companies turn ambitious AI and digitalization strategies into production-grade software - and you take end-to-end ownership of that delivery for our most complex client engagements, while setting the engineering standard that elevates the entire Engineering team. Whether your depth comes from AI/ML systems, large-scale digitalization programs, or solution architecture for complex enterprise environments, you thrive on turning ambiguity into scalable, well-governed systems. Your tasks will include: * Architecting and implementing production-grade software and AI solutions for enterprise clients - spanning classical ML, GenAI applications, validated RAG, and agentic systems, alongside the broader digital and software architecture around them - with attention to security, scalability, hybrid/cloud deployments, and operational maturity * Defining and championing engineering excellence across the team: code quality, design reviews, evaluation harnesses, observability, security, and MLOps standards * Leading technical delivery from target architecture through production hardening and client handover, working closely with engagement leads on scope and value * Building reusable engineering accelerators - templates, libraries, and evaluation frameworks - that multiply the impact of the wider Engineering team * Mentoring mid-level and senior engineers, facilitating technical guilds, and driving a culture of shared knowledge and continuous improvement DEIN PROFIL * 10+ years of software engineering experience, including a strong track record at principal or lead level - as an AI/ML engineer, software architect, digitalization lead, or solution architect - with meaningful exposure to AI/ML systems in production or a demonstrated ability to grow quickly into that depth * Deep engineering foundation across distributed systems, APIs, data pipelines, cloud-native architecture (Azure, AWS, or GCP), containers, CI/CD, and MLOps * Strong command of Python and solid exposure to the modern AI stack - LangChain/LangGraph, vector stores, evaluation frameworks, or platforms such as Azure AI Foundry - or a proven ability to master this stack rapidly given your engineering depth * A demonstrable track record leading complex, end-to-end technical delivery in client-facing settings, at enterprise scale * Pragmatic and code-first in your approach; opinionated about quality, evaluation, security, and operational maturity * Fluent in both English and German DEINE VORTEILE * A highly qualified and motivated team of ~90 people is on a journey to change the rapidly evolving European AI Landscape * Experience the best of both worlds with our hybrid work model: You can choose to work from our vibrant offices - either at the IPAI in Heilbronn or the House of Communication in Munich - while also enjoying the flexibility to work remotely a few days each week * Opportunity to shape a variety of projects and the development of new, original content based on the latest developments in AI and its adoption in businesses * An atmosphere that encourages to think and experiment in new ways with software, hardware, and processes * A highly visible initiative that helps you build a large and high-level network of start-ups, partners, and tech companies * A flexible development budget that’s yours to shape - invest it in training, certifications, conferences, or new challenges, however you want to grow * Sports membership with Wellpass to access thousands of sports facilities all over Germany (and beyond), as well as online courses * JobRad: Lease a bike for a cheaper rate via JobRad and we cover the bike insurance on top * Sabbatical option: You can take a sabbatical of up to 3 months after min. 3 years of employment - because sometimes 30 vacation days are not enough to explore the beauty of this world * PME Familienservice: A 24/7 support for a successful work & life in any life situation. Benefit from free support in areas like life coaching, child care and many other options * Mobility budget: Every month we contribute to your individual mobility usage with public transport or shared mobility offers within the app Moovster * Workation: Work from anywhere in the EU/EWR area for up to 3 months per year - combining working at a nice place and spending your leisure time in the evening like vacation KONTAKT Lucas Fernandes - Senior Talent Acquisition Specialist appliedAI Initiative GmbH, August-Everding-Str. 25, 81671 München