Principal IT Systems Administrator
CarGurus•Boston, MA
•Hybrid
About The Position
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.
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 Haves
- 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
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.
Benefits
- Equity for all employees, both when they start and as they continue to grow with us.
- Career development programs
- 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
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What This Job Offers
Job Type
Full-time
Career Level
Principal
Education Level
No Education Listed
