Senior IT Service Desk Analyst

Car Gurus • Boston, MA

45d • $71,000 - $90,000 • Hybrid

About The Position

CarGurus is hiring a Senior IT Service Desk Analyst to join our Global IT Team. We're seeking a highly skilled, technically versatile, and customer-focused Senior IT Engineer who thrives on solving complex challenges, driving operational excellence, and enabling innovation across our technology landscape. This role requires someone who can balance hands-on technical depth with strong critical thinking, mentorship, and process improvement skills. This position is hybrid out of our Boston, MA office. This role includes regular physical activity such as moving through the office to provide support, transporting and deploying IT equipment, and performing setup or troubleshooting in confined spaces. All tasks must be performed safely and efficiently.

Requirements

• 5+ years of progressive IT experience, including at least 2 years in a senior or 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, PowerShell, 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 (IAM) solutions (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.
• Associate's or Bachelor's degree in Information Systems, Computer Science, or related field-or equivalent professional experience.

Nice To Haves

• Relevant certifications (e.g., CompTIA A+/Network+, ITIL Foundation, Jamf Certified Tech/Admin, Microsoft Certified: Modern Desktop Administrator, or equivalent) strongly preferred.

Responsibilities

• 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, ensuring timely resolution and root cause documentation.
• Mentor and provide technical leadership to junior team members, fostering skill development, knowledge sharing, and adherence to ITIL-aligned best practices.
• Drive incident, problem, and change management processes, ensuring high-impact issues are properly communicated, escalated, and resolved with minimal business disruption.
• Develop, document, and maintain technical runbooks, knowledge base articles, and automation scripts to improve efficiency and scalability of IT operations.
• Lead proactive service improvement initiatives, using metrics and feedback to optimize user experience, performance, and reliability.
• Manage and support enterprise collaboration and endpoint management tools, including MDM (e.g., Jamf, Intune), identity platforms (SailPoint/Okta), and remote access solutions (VPN, VDI).
• Administer and support SaaS and cloud applications such as Google Workspace, Microsoft 365, Slack, and other business-critical tools.
• Implement and maintain endpoint security and compliance standards, working closely with the Security team to ensure data integrity and regulatory compliance.
• Contribute to strategic IT projects, such as office builds, infrastructure refreshes, and technology rollouts, collaborating with vendors and internal stakeholders.
• 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, PowerShell, JavaScript, etc.) to streamline onboarding, patching, and asset lifecycle management.
• Manage user lifecycle processes including onboarding, offboarding, and access control, ensuring compliance with governance policies.
• Participate in on-call rotation and provide after-hours support when required to maintain operational continuity.

Benefits

• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Industry: Publishing Industries
• Education Level: Associate degree
• Number of Employees: 1,001-5,000 employees