Hiring: Principal IT Systems Administrator Company: CarGurus Location: Boston, MA Job Posted Time: 2026-09-15 11:11:37 Employment Type: Hybrid Target Skills & Keywords : Configuration Management, Okta, PowerShell, Python, SOC 2, SaaS, Systems Engineering, Terraform, VPN, macOS About the job Experience: •8+ years) in IT systems engineering/administration, with significant time in senior/lead roles on enterprise-scale environments. Required Skills: •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. •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. •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. Qualifications: •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. •A bias toward ownership, documentation, and mentorship. •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). Compensation: •$113,000 - $142,000 / year Interested candidates, please apply directly through the job posting on company's career page or try via AI auto apply on this platform. Don't miss this opportunity to join a forward-thinking team!