Senior IT Service Desk Analyst

Role Overview

Car Gurus is hiring a Senior IT Service Desk Analyst to join our Global IT Team. The position is hybrid out of our Boston, MA office and requires someone who can balance technical depth with critical thinking, mentorship, and process improvement skills.

• Demonstrate flexibility to cope with changing demands based on business priority.
• Serve as the senior escalation point for complex technical issues across endpoints, network connectivity, application support, and identity management.
• Mentor junior team members, fostering skill development, knowledge sharing, and adherence to ITIL‑aligned best practices.
• Drive incident, problem, and change management processes with effective communication and minimal business disruption.
• Develop, document, and maintain technical runbooks, knowledge base articles, and automation scripts to improve efficiency and scalability.
• Lead proactive service improvement initiatives using metrics and feedback to optimize user experience, performance, and reliability.
• Manage enterprise collaboration and endpoint management tools, including MDM (Jamf, Intune) and identity platforms (Okta, SailPoint).
• Administer and support SaaS and cloud applications such as Google Workspace, Microsoft 365, Slack, and other critical business tools.
• Implement and maintain endpoint security and compliance standards in collaboration with the Security team.
• Contribute to strategic IT projects such as office builds, infrastructure refreshes, and technology rollouts.
• Monitor technology trends and make recommendations for adoption or integration of innovative solutions aligned with business and security objectives.
• Develop and deploy automation tools and scripts (Python, Power Shell, JavaScript, etc.) for onboarding, patching, and asset lifecycle management.
• Manage user lifecycle processes including onboarding, offboarding, and access control in compliance with governance policies.
• Participate in on‑call rotation and provide after‑hours support when required to maintain operational continuity.

• 5+ years of progressive IT experience, including at least 2 years in a senior escalation role within a corporate Service Desk or Desktop Engineering environment.
• Deep expertise in macOS, Windows, and Linux administration, including endpoint management, imaging, and configuration.
• Strong scripting and automation skills (Python, Power Shell, Bash, JavaScript) for workflow automation, system monitoring, and reporting.
• Hands‑on experience with enterprise management tools such as Jamf Pro and Intune.
• Proficiency with identity and access management (Okta, or similar), MFA, and SSO implementations.
• Familiarity with networking fundamentals, including DNS, DHCP, VPNs, and VLANs, with the ability to troubleshoot connectivity and performance issues.
• In‑depth understanding of ITIL processes and experience implementing Service Management best practices via Jira Service Management or similar ITSM platforms.
• Strong analytical and problem‑solving abilities, with the capability to perform detailed root cause analyses and propose preventive measures.
• Exceptional communication skills, able to interface confidently with executive leadership and non‑technical users alike.
• Proactive mindset with demonstrated ability to lead projects, improve systems, and influence IT strategy through data‑driven insights.
• Relevant certifications (e.g., CompTIA A+/Network+, ITIL Foundation, Jamf Certified Tech/Admin, Microsoft Certified: Modern Desktop Administrator, or equivalent) strongly preferred.
• Associate’s or Bachelor’s degree in Information Systems, Computer Science, or related field—or equivalent professional experience.

Position Pay Range: $71,000—$90,000 USD. Individual pay is determined by work location and other factors such as job‑related skills, experience, and relevant education or training. The annual base salary forms part of a comprehensive Total Rewards Package, with potential discretionary bonuses and Restricted Stock Units (RSUs).

We reward our Gurus with best‑in‑class benefits and compensation, including equity, a flexible hybrid model, robust time‑off policies, daily free lunch, new…