Systems Administrator I

Winter Services; Milwaukee (WI); On-site; USD 65,000 - 80,000; Full time

Job summary

Winter Services in Milwaukee, WI is seeking a Systems Administrator I to support the IT infrastructure, security, and reliability. You will assist with day-to-day administration, troubleshoot issues, manage access, and help implement upgrades and security initiatives.

Under the VP of Technology, you will build technical expertise, expand responsibilities, and contribute to projects across networking, endpoints, and cloud services.

Qualifications

• 3+ years in IT support or systems administration.
• Experience with Windows operating systems.
• Experience managing Microsoft 365 and user accounts.
• Knowledge of AD, Entra ID, and access management.

Responsibilities

• Assist with administration and maintenance of IT infrastructure.
• Manage user accounts, permissions, and security groups.
• Support Intune-based device configuration and patching.
• Monitor system health and troubleshoot escalated issues.
• Coordinate with vendors and assist with backups and recovery.
• Document system configurations and procedures.

Job description

The Systems Administrator I supports the administration, maintenance, security, and reliability of the organization's IT infrastructure and technology environment. This position is responsible for assisting with day-to-day systems administration, troubleshooting technical issues, maintaining user access, and supporting the organization's infrastructure and security initiatives.

Working under the direction of the VP of Technology, this role provides an opportunity to develop technical expertise and take on increasing responsibility for systems, infrastructure, and technology projects. The ideal candidate has a solid foundation in IT support and administration, strong troubleshooting abilities, and an interest in expanding their technical skills.

Essential Functions

• Assist with the administration, maintenance, and troubleshooting of workstations, network equipment, phones, and related IT infrastructure.
• Administer Microsoft 365 services, including Exchange Online, Entra ID, SharePoint, OneDrive, and Teams.
• Manage user accounts, permissions, security groups, and access controls across organizational systems.
• Support device configuration, deployment, patching, and ongoing management using Microsoft Intune and other administrative tools.
• Monitor system health, availability, and performance, escalating issues as appropriate.
• Assist with network administration, including troubleshooting connectivity, wireless networks, and related infrastructure.
• Support endpoint security, antivirus, monitoring, and vulnerability remediation activities.
• Assist with backup monitoring, recovery procedures, and business continuity initiatives.
• Troubleshoot and resolve escalated technical issues involving hardware, software, operating systems, and network connectivity.
• Support employee onboarding and offboarding processes, including account provisioning, equipment preparation, and access management.
• Maintain accurate documentation of system configurations, administrative procedures, network infrastructure, and technical processes.
• Assist with technology upgrades, system migrations, infrastructure improvements, and other departmental projects.
• Coordinate with external technology vendors and service providers as needed.
• Identify opportunities to improve system reliability, security, efficiency, and standardization.
• Follow established IT policies, security standards, and change management procedures.
• Perform other related duties as assigned.

Qualifications

• 3 years or more of experience in IT support, systems administration, or a related technical role.
• Working knowledge of Windows operating systems.
• Experience supporting Microsoft 365 and user account administration.
• Familiarity with Active Directory, Entra ID, and user access management.
• Foundational understanding of networking concepts, including TCP/IP, DNS, DHCP, and VPN connectivity.
• Experience troubleshooting hardware, software, and network-related issues.
• Strong analytical, organizational, and problem-solving skills.
• Ability to work independently on routine tasks while recognizing when guidance or escalation is appropriate.
• Strong communication skills and the ability to work effectively with technical and non-technical personnel.
• Willingness to learn new technologies and develop additional technical skills as needed to support organizational needs