Senior IT Service Desk Analyst

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 ~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!
Role overview
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.
What you'll do

• 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.

What you'll bring

• 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.
• 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.

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
$71,000 - $90,000 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