The Principal IT Systems Administrator oversees IT systems leading complex initiatives managing infrastructures and endpoints enhancing security compliance and ensuring incident management and documentation standards are met.

Who we are
At CarGurus (NASDAQ: CARG) our mission is to give people the power to reach their destination. We started as a small team of developers determined to bring trust and transparency to car shopping. Since then our history of innovation and go-to-market acceleration has driven industry-leading growth. In fact we're the largest and fastest-growing automotive marketplace and we've been profitable for over 15 years.
What we do
The market is evolving and we are too moving the entire automotive journey online and guiding our customers through every step. That includes everything from the sale of an old car to the financing purchase and delivery of a new one. Today tens of millions of consumers visit CarGurus.com each month and ~30000 dealerships use our products. But they're not the only ones who love CarGurus-our employees do too. We have a people-first culture that fosters kindness collaboration and innovation and empowers our Gurus with tools to fuel their career growth. Disrupting a trillion-dollar industry requires fresh and diverse perspectives. Come join us for the ride!
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.
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.
What you'll do

• 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.

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).
Position Pay Range
$113000 - $142000 USD
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