Systems Administrator II

About the role

This position involves maintaining and improving the internal systems and services that support the daily operations of our staff. You will manage identity, collaboration, and networking infrastructure to ensure a reliable and secure environment for all employees. In this role, you will own the maintenance and enhancement of enterprise systems that keep the organization running efficiently. You will be responsible for the reliable operation of identity, collaboration, and networking services. The position requires a proactive approach to ensuring system uptime and security compliance. You will partner closely with security and business teams to align technology services with organizational objectives. This role demands ownership of complex technical issues from initial identification through full resolution. Your work will directly impact the productivity of all staff by providing stable and secure digital tools.

Key facts

What you'll do

• Administer core enterprise systems and collaboration platforms to maintain service reliability.
• Manage identity tasks in Okta or similar platforms, including user provisioning, access changes, and login support.
• Maintain collaboration tools such as Slack, Google Workspace, and Microsoft 365 to ensure seamless communication.
• Enforce security standards through MFA and access control management to protect corporate resources.
• Oversee office network services, VPN, and ZTNA remote access solutions for secure connectivity.
• Resolve technical issues related to identity, connectivity, and software tools with a methodical approach.
• Execute system maintenance, patching, and configuration updates to mitigate risks and improve performance.
• Develop and update technical documentation and knowledge base articles for processes and troubleshooting.
• Participate in sprint-based planning sessions to balance project deliverables with operational support needs.
• Join an on-call rotation as required to address critical incidents and provide timely response.

Requirements

• 3+ years of professional experience in IT operations, systems administration, or enterprise application support.
• Practical experience with Okta or equivalent identity management platforms for managing user access.
• Proficiency in supporting Slack, Google Workspace, and Microsoft 365 across diverse user environments.
• Experience with enterprise networking, VPN, and ZTNA technologies to enable secure remote access.
• Strong ability to troubleshoot and resolve complex technical problems through systematic analysis.
• Familiarity with user lifecycle management, SSO, and MFA processes to maintain security posture.
• Ability to manage multiple tasks and priorities effectively in a fast-paced operational setting.
• Strong written and verbal communication skills for interacting with technical and non-technical stakeholders.
• Ability to collaborate across IT, Security, and business departments to align on goals and initiatives.
• Willingness to participate in an on-call rotation and respond to off-hours system alerts as needed.

Skills & tools

• Okta
• Slack
• Google Workspace
• Microsoft 365
• VPN
• ZTNA
• Identity and Access Management (IAM)
• MFA
• SSO
• System administration
• Network services
• Troubleshooting
• Documentation
• Sprint planning
• On-call support

Practical notes

This role offers a total rewards package including equity, discretionary bonuses, and RSUs. Benefits include a flexible hybrid work model, daily free lunch, commuting cost coverage, a new car discount, and access to fitness and meditation apps. CarGurus may request in-person interviews in Boston; candidates are responsible for their own travel expenses for these meetings. Employment is contingent on successful completion of any required background checks and verification of credentials. The position requires the ability to work full-time hours as specified in the engagement details. Candidates must be legally authorized to work in the United States without sponsorship for this role. The work location is fixed in Boston, Massachusetts, and remote work arrangements are defined by the hybrid model. CarGurus maintains the right to modify tools, processes, and responsibilities to align with evolving business needs. All team members are expected to adhere to company policies and standards. Participation in ongoing training is encouraged to keep skills current with technology trends. The role contributes to the overall infrastructure stability of the organization.