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Boston, Massachusetts, United States Hybrid Full-time USD 113,000 – 142,000 / year

CarGurus is hiring a Principal IT Systems Administrator

Responsibilities

  • Design and implement complex configurations for core IT platforms (identity, collaboration, infrastructure, SaaS).
  • Establish configuration management, lead performance/reliability improvements, and automate repetitive tasks.
  • Design enterprise-wide endpoint strategies (macOS, Windows, mobile).
  • Develop and enforce security policies, automate software/OS deployments via MDM/EMM, and own compliance reporting.
  • 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).
  • 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.
  • Define and implement incident response strategies, lead Post-Incident Reviews (PIRs) to drive corrective action, develop runbooks, and oversee on-call rotations.
  • Define documentation standards (architecture, SOPs, runbooks) and ensure knowledge bases are accurate, comprehensive, and easily discoverable.

Requirements

  • 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)
  • Experience partnering with Security Engineering and GRC

Benefits

  • Equity for all employees, both when they start and as they continue to grow with us.
  • Best-in-class benefits and compensation.
  • Career development and corporate giving programs.
  • Employee resource groups (ERGs) and communities.
  • Flexible hybrid model.
  • Robust time off policies.
  • Daily free lunch.
  • New car discount.
  • Meditation and fitness apps.
  • Commuting cost coverage.

Work Arrangement

Hybrid — Boston, Dublin

Additional Information

  • In-person interviews may be required, particularly for positions based in Boston and Dublin offices.
  • Travel expenses are the responsibility of the candidate.
  • Accommodations available upon request for candidates with disabilities.
  • No discrimination based on race, color, religion, national origin, age, sex, marital status, ancestry, physical or mental disability, veteran status, gender identity, or sexual orientation.
About company
CarGurus
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. 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
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Job Details
Department Engineering & Technology
Category infrastructure
Posted 8 days ago