Junior Systems Administrator - IT Infra & Security

Winter Services, LLC; Milwaukee (WI); On-site; USD 55,000 - 75,000; Full time

Job summary

Winter Services, LLC is seeking a Systems Administrator I to help manage the IT infrastructure, keep systems reliable, and support security initiatives. The role collaborates with the VP of Technology to handle day-to-day administration, troubleshooting, and documentation.

You'll work on Microsoft 365, AD, Entra ID, Intune, and network basics while supporting onboarding, backups, and incident resolution. A solid IT support background and curiosity to grow technically are key.

Qualifications

• 3+ years of experience in IT support or systems administration.
• Working knowledge of Windows operating systems.
• Experience with Microsoft 365 and user account administration.
• Familiarity with Active Directory, Entra ID, and user access management.
• Foundational networking concepts: TCP/IP, DNS, DHCP, VPN.
• Experience troubleshooting hardware, software, and network issues.
• Strong analytical, organizational, and problem-solving skills.
• Ability to work independently and escalate when needed.
• Strong communication skills with technical and non-technical colleagues.
• Willingness to learn new technologies to support organizational needs.

Responsibilities

• Assist with administration, maintenance, and troubleshooting of IT infrastructure.
• Administer Microsoft 365 services including Exchange Online and Entra ID.
• Manage user accounts, permissions, and access controls.
• Support device configuration using Microsoft Intune and other tools.
• Monitor system health, uptime, and performance, escalating issues.
• Assist with network administration and connectivity troubleshooting.
• Support endpoint security, antivirus, monitoring, and remediation activities.
• Assist with backup monitoring, recovery procedures, and continuity initiatives.
• Document system configurations and procedures accurately.
• Assist with upgrades, migrations, and infrastructure projects.
• Coordinate with external vendors as needed.
• Identify opportunities to improve reliability, security, and efficiency.

Skills

3+ years IT support experience

Independent working

Analytical problem-solving

Strong communication

Willingness to learn

Tools

Windows OS

Microsoft 365

Entra ID

Active Directory

Microsoft Intune

VPN connectivity

Job description

Winter Services, LLC is seeking a Systems Administrator I to help manage the IT infrastructure, keep systems reliable, and support security initiatives. The role collaborates with the VP of Technology to handle day-to-day administration, troubleshooting, and documentation.

You'll work on Microsoft 365, AD, Entra ID, Intune, and network basics while supporting onboarding, backups, and incident resolution. A solid IT support background and curiosity to grow technically are key.