Cargurus Inc.

Cargurus Inc.

Principal IT Systems Administrator

Boston, Massachusetts, United States · Principal

Sponsorship not specified$113k-$142kDetected 75 days ago
PythonPowerShellTerraformCybersecurityIncident ResponseComplianceSystems EngineeringVPNCommunicationCollaboration

About the role

  • 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.

Responsibilities

  • 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.
  • Extensive experience (typically 8+ years) in IT systems engineering/administration, with significant time in senior/lead roles on enterprise-scale environments.
  • Demonstrated ability to design complex configurations, lead large cross-functional projects, and influence architectural decisions.
  • Design and implement complex configurations for core IT platforms (identity, collaboration, infrastructure, SaaS).

Requirements

  • Strong automation mindset and proficiency with scripting/infrastructure-as-code (Python, PowerShell, Terraform).
  • Proven track record leading major incidents and PIRs.
  • Experience in environments with security, regulatory, or audit requirements (SOC 2, SOX).

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.
  • Working at CarGurus
  • Candidates selected for an in-person interview will be notified in advance.
  • Please be aware that travel expenses are the responsibility of the candidate.
  • 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 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.

Skills

  • Since then, our history of innovation and go-to-market acceleration has driven industry-leading growth.
  • 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 ~30,000 dealerships use our products.
  • But they're not the only ones who love CarGurus-our employees do, too.
  • Disrupting a trillion-dollar industry requires fresh and diverse perspectives.
  • Come join us for the ride!

Compensation

  • The displayed range represents the expected annual base salary / On-Target Earnings (OTE) for this position.

Company info

  • 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 ~30,000 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!
  • 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.
  • In fact, we're the largest and fastest-growing automotive marketplace, and we've been profitable for over 15 years.
  • The market is evolving, and we are too, moving the entire automotive journey online and guiding our customers through every step.
  • We have a people-first culture that fosters kindness, collaboration, and innovation, and empowers our Gurus with tools to fuel their career growth.
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This listing is sourced directly from Cargurus Inc.'s careers page and normalized into a canonical job model.