Principal IT Systems Administrator

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, and mentorship.

Nice to have: Experience in a high-growth SaaS or technology company, familiarity with CarGurus tools (Okta, Google Workspace/M365, Jamf, Intune), and experience partnering with Security Engineering and GRC.

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).

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.

CarGurus may require in-person interviews as part of our hiring process, particularly for positions based in our Boston and Dublin offices.

Candidates selected for an in-person interview will be notified in advance.

Please be aware that travel expenses are the responsibility of the candidate.

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