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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