Systems Administration II

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
As a System Administrator II, you will help support and improve the core systems and services our employees use every day. You will work across identity, collaboration tools, office networking, and remote access technologies to help deliver a secure, reliable, and seamless employee experience.
This role is ideal for someone who enjoys a mix of operational support and project work, is comfortable troubleshooting across multiple platforms, and thrives in a fast-paced environment. You will play an important role in supporting key systems including Okta, Slack, Google Workspace, Microsoft 365, and remote access solutions such as VPN and ZTNA.
What you'll do

• Support and administer core enterprise systems and collaboration platforms across the business
• Manage day-to-day administration of Okta or a similar identity platform, including user provisioning, access changes, group management, and login troubleshooting
• Support collaboration tools including Slack, Google Workspace, Microsoft 365, and related business applications
• Help maintain secure access controls, MFA, and other identity and access management best practices
• Support office network services and remote access tools, including Wi-Fi, VPN, and ZTNA solutions
• Troubleshoot employee issues across identity, collaboration tools, network connectivity, and remote access
• Perform regular maintenance, upgrades, patching, and configuration changes across managed platforms
• Create and maintain documentation, runbooks, and knowledge base content
• Contribute to projects that improve reliability, user experience, and operational efficiency
• Work within a sprint-based planning model while balancing project work and day-to-day support needs
• Participate in an on-call rotation as needed

What you'll bring

• 3+ years of experience in systems administration, IT operations, or enterprise application support
• Hands-on experience with Okta or a similar identity and access management platform
• Experience supporting collaboration tools such as Slack, Google Workspace, and Microsoft 365
• Experience supporting enterprise networking and remote access solutions, including VPN and/or ZTNA
• Strong troubleshooting and problem-solving skills
• Experience with user lifecycle management, SSO, MFA, and access management processes
• Strong organizational skills and the ability to manage multiple priorities
• Strong written and verbal communication skills
• Ability to work cross-functionally with IT, Security, and business stakeholders
• Willingness to participate in an on-call rotation

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
$84,000 - $105,000 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.
CarGurus may require in-person interviews as part of our hiring process, particularly for positions based in our Boston and Dublin offices. Candidates selected for an in-person interview will be notified in advance. Please be aware that travel expenses are the responsibility of the candidate.
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