Windows System Administrator

Red Oak Technologies; Elkhart (IN); On-site; USD 80,000 - 100,000; Full time

Job summary

Red Oak Technologies in Elkhart, IN is seeking a Windows Systems Administrator to join a growing internal IT team. This is a hands-on role focusing on server, cloud identity, and infrastructure administration rather than a traditional help desk position.

The successful candidate will own Microsoft environments, manage Windows Server, Microsoft 365, Intune, and virtualization, and drive improvements across security and operations.

Qualifications

• Hands-on Microsoft systems administration experience.
• Experience with Microsoft 365 beyond basic end-user support.
• Experience managing Windows Server environments.
• Strong troubleshooting and problem-solving skills.
• Ability to own technical issues and drive to resolution.
• Strong communication with technical and non-technical users.
• Willingness to learn new technologies.

Responsibilities

• Administer and support Microsoft Windows Server and Microsoft 365 environments.
• Perform hands-on administration within the Microsoft 365 tenant.
• Manage users, permissions, policies, identity, and Microsoft-based infrastructure.
• Support Microsoft Intune and endpoint management.
• Build, configure, maintain, and troubleshoot virtual machines and virtualization environments.
• Participate in virtualization infrastructure and migration initiatives.
• Troubleshoot complex Windows, server, application, and infrastructure issues.
• Support security and identity initiatives across the IT environment.
• Evaluate existing systems and recommend infrastructure improvements.
• Take ownership of assigned IT projects from troubleshooting through implementation.
• Partner with internal IT team members and business users to deliver effective solutions.

Skills

MS systems admin

Troubleshooting

Communication

Ownership

PowerShell scripting

Tools

VMware

Hyper-V

XenServer

PowerShell

Job description

Location: Elkhart, IN – 100% Onsite is required.

Salary: $80- 100,000 Base Salary DOE

Overview

We are seeking a Windows Systems Administrator to join a growing internal IT team in Elkhart, Indiana.

This is a hands‑on systems administration role — not a traditional help desk or desktop support position. We are looking for someone who has real‑world experience administering Microsoft environments and wants the opportunity to take greater ownership of systems, infrastructure, virtualization, security, and IT projects.

We are open to both experienced Systems Administrators and motivated, developing administrators who have a strong Microsoft foundation and are eager to continue expanding their technical skills.

Responsibilities

• Administer and support Microsoft Windows Server and Microsoft 365 environments
• Perform hands‑on administration within the Microsoft 365 tenant
• Manage users, permissions, policies, identity, and Microsoft‑based infrastructure
• Support Microsoft Intune and endpoint management
• Build, configure, maintain, and troubleshoot virtual machines and virtualization environments
• Participate in virtualization infrastructure and migration initiatives
• Troubleshoot complex Windows, server, application, and infrastructure issues
• Support security and identity initiatives across the IT environment
• Evaluate existing systems and recommend infrastructure improvements
• Take ownership of assigned IT projects from troubleshooting through implementation
• Partner with internal IT team members and business users to deliver effective solutions

Required Qualifications

• Hands‑on Microsoft systems administration experience
• Experience administering Microsoft 365 beyond basic desktop or end‑user support
• Experience working with Windows Server environments
• Strong troubleshooting and problem‑solving skills
• Ability to independently take ownership of technical issues and drive them through resolution
• Strong communication skills and ability to work effectively with technical and non‑technical users
• Initiative and desire to continue developing technically

Preferred Qualifications

• Hands‑on virtualization experience with VMware, Hyper‑V, XenServer, or similar technologies
• Experience creating, configuring, maintaining, or migrating virtual machines
• PowerShell scripting or automation experience
• Okta or other identity management experience
• Exposure to infrastructure security or cybersecurity initiatives

What We’re Looking For

We value hands‑on experience over simply having exposure to a technology. The ideal candidate can clearly speak to systems they have personally administered, configured, built, migrated, or troubleshot.

You should be someone who:

• Takes ownership and works effectively with minimal supervision
• Approaches technical problems methodically and communicates solutions clearly
• Is proactive, curious, and willing to learn new technologies
• Is comfortable using modern tools, including automation and AI‑assisted technologies
• Wants to continue growing into more advanced systems, infrastructure, engineering, or security responsibilities

Candidates earlier in their systems administration careers are encouraged to apply. A strong foundation in Microsoft administration is most important; additional training and development can be provided in areas such as virtualization and other infrastructure technologies.