Principal IT Systems Administrator

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, leads complex initiatives, serves as a top escalation point, and partners across the business to ensure infrastructure and endpoints enable productivity while meeting security and compliance needs.

• Design and implement complex configurations for core IT platforms (identity, collaboration, infrastructure, SaaS), establish configuration management, lead performance and 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 such as migrations and 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), develop runbooks, and oversee on‑call rotations.
• Define documentation standards (architecture, SOPs, runbooks) and ensure knowledge bases are accurate, comprehensive, and easily discoverable.

• 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/as‑code tools (Python, Power Shell, 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 Car Gurus tools (Okta, Google Workspace/M365, Jamf, Intune), and experience partnering with Security Engineering and GRC.

Position Pay Range: $113,000—$142,000 USD. 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).

Car Gurus strives to be a place where 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.