Systems Administrator II

Cargurus

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

Cargurus

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. WHAT YOU’LL DO * Design and build AI-powered workflows and agent-based systems that transform how teams operate across the company. * Partner directly with stakeholders in revenue, product, engineering, finance, and operations to gather requirements, map existing workflows, and identify high-leverage opportunities for AI. * Build end-to-end — from scoping and architecture through implementation and deployment. This team ships, it doesn’t hand off specs. * Work with AI APIs and platforms (Anthropic/Claude, AWS Bedrock, and others) to build agentic systems, automation pipelines, and intelligent tooling. * Operate across a messy, heterogeneous environment — AWS infrastructure, Salesforce, internal services — without waiting for everything to be clean before you start building. * Help shape the technical strategy and standards for AI Solutions as a function. WHAT YOU’LL BRING Must-haves: * 8+ years of relevant software engineering experience (no degree required; equivalent experience is fully accepted). * Strong software engineering fundamentals — you’ve built and shipped production systems, not just prototypes. * Proficiency in Python as the primary language for this work; comfort with additional languages is a plus. * Experience designing APIs, services, and data pipelines. You think in systems, not scripts. * AWS fluency — you’re comfortable working within AWS infrastructure and services. * Hands-on experience building with LLM APIs, agent frameworks, or AI-powered applications — not just experimentation, but something that ran in production or was used by real people. * Ability to operate with high autonomy. You’ll scope your own work, make architectural decisions, and own outcomes. * Willingness to work across the full stack of a business — including systems like Salesforce that aren’t glamorous but are where the high-impact problems live. Nice-to-haves: * Experience with workflow orchestration or automation at scale. * Familiarity with Salesforce APIs and integration patterns (not Salesforce administration). * Background in recommendations, search, data science, or ML engineering. * Experience working cross-functionally with non-technical stakeholders. 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 $144,000—$172,000 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

Cargurus

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. What you'll do * Design and build AI-powered workflows and agent-based systems that transform how teams operate across the company. * Partner directly with stakeholders in revenue, product, engineering, finance, and operations to gather requirements, map existing workflows, and identify high-leverage opportunities for AI. * Build end-to-end — from scoping and architecture through implementation and deployment. This team ships, it doesn’t hand off specs. * Work with AI APIs and platforms (Anthropic/Claude, AWS Bedrock, and others) to build agentic systems, automation pipelines, and intelligent tooling. * Operate across a messy, heterogeneous environment — AWS infrastructure, Salesforce, internal services — without waiting for everything to be clean before you start building. * Help shape the technical strategy and standards for AI Solutions as a function. What you'll bring * 5+ years of relevant software engineering experience. * Strong software engineering fundamentals — you’ve built and shipped production systems, not just prototypes. * Proficiency in Python as the primary language for this work; comfort with additional languages is a plus. * Experience designing APIs, services, and data pipelines. You think in systems, not scripts. * AWS fluency — you’re comfortable working within AWS infrastructure and services. * Hands-on experience building with LLM APIs, agent frameworks, or AI-powered applications — not just experimentation, but something that ran in production or was used by real people. * Ability to operate with high autonomy. You’ll scope your own work, make architectural decisions, and own outcomes. * Willingness to work across the full stack of a business — including systems like Salesforce that aren’t glamorous but are where the high-impact problems live. Nice-to-haves: * Experience with workflow orchestration or automation at scale. * Familiarity with Salesforce APIs and integration patterns (not Salesforce administration). * Background in recommendations, search, data science, or ML engineering. * Experience working cross-functionally with non-technical stakeholders.   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 $144,000—$181,000 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