IT Support Specialist

Phoenix Investors • Milwaukee, WI

We are seeking an IT Support Specialist (Level 1/2) to join our growing team. Unlike a traditional help desk role, this position emphasizes collaboration, ownership from start to finish, and clear communication and documentation. The ideal candidate brings strong end-user support experience, a customer-focused mindset, structured troubleshooting skills, and a curiosity for continuous improvement. This is an on-site role based in our Milwaukee office; remote work is not available.

This role serves as the frontline of IT service delivery, responsible for delivering a high-quality end-user experience across devices, applications, and access services. The IT Support Specialist owns initial troubleshooting and resolution while ensuring accurate documentation and appropriate escalation.

  • Provide technical support for end users across devices, applications, and access.
  • Troubleshoot and resolve Tier 1 and Tier 2 issues in Microsoft 365 and Windows environments.
  • Manage support requests and documentation in the ITSM platform.
  • Configure, deploy, and maintain laptops, desktops, and peripheral devices.
  • Support onboarding and offboarding processes, including accounts, access, and devices.
  • Escalate issues with complete diagnostic information and context.
  • Contribute to the knowledge base and documentation to reduce repeat issues.
  • Collaborate with the IT team and support operational and project-based work.
  • Other duties may be assigned as necessary to support IT operations and business needs.
  • Delivers consistent, professional support to end users.
  • Resolves issues or escalates cleanly with full documentation.
  • Maintains clear, repeatable documentation for support processes.
  • Contributes to reducing repeat issues through standardization.
  • Works collaboratively across the IT team.

AI and Automation Expectations

  • Demonstrates an interest in improving efficiency through tools and automation.
  • Utilizes technology to reduce repetitive work where appropriate.
  • Approaches problems with a mindset focused on standardization and scalability.

Required Qualifications

  • 1 – 3+ years of IT support or help desk experience.
  • Experience supporting Microsoft 365 (Outlook, Teams, SharePoint, OneDrive).
  • Strong troubleshooting capability in Windows environments.
  • Experience working within a ticketing or ITSM system.
  • Strong written and verbal communication skills.

Preferred Qualifications

  • Experience with Intune or modern endpoint management.
  • Exposure to identity and access management (MFA, permissions, provisioning).
  • Basic networking knowledge (Wi-Fi, VPN, connectivity).
  • Experience working within SLA-driven support environments.
  • Experience documenting processes or contributing to knowledge bases.

Phoenix offers comprehensive benefits, company-paid parking, and daily breakfast and lunch prepared by our on-site chefs, all designed to make your workday easier and more enjoyable.

  • 401(k) with employer match
  • Medical, dental, and vision insurance
  • Paid time off (PTO) and holidays
  • Company-paid parking
  • Company-paid breakfast and lunch

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