IT Support Specialist

Onsite | Chicago, IL | Full-Time | Excellent Benefits

Are you a hands‑on IT professional who enjoys troubleshooting technology, supporting users, and helping keep systems running smoothly?

Labelmaster is seeking an IT Support Specialist to provide day-to-day technical support across the organization. In this role, you will troubleshoot hardware and software issues, support Microsoft 365 applications, manage user accounts, deploy equipment, and help maintain a secure and reliable technology environment.
Labelmaster's mission is to simplify Dangerous Goods (Hazmat) compliance and shipping, helping make the world a safer place. Join our team and play a critical role in supporting the technology that keeps our business moving forward.

• Provide technical support for desktops, laptops, mobile devices, printers, and peripherals.
• Install, configure, maintain, and troubleshoot hardware and software.
• Support employee onboarding, offboarding, password resets, and access management.
• Assist with Microsoft 365 administration, including Outlook, Teams, One Drive, and SharePoint.
• Respond to help desk requests and document resolutions in the ticketing system.
• Support IT security initiatives, software updates, and endpoint protection.
• Manage IT inventory, equipment deployment, and lifecycle replacement activities.
• Assist with system upgrades, technology improvements, and special IT projects.

Required

• Minimum of 4 years of experience supporting Windows-based environments.
• Experience with Windows 11 and Windows Server environments.
• Strong knowledge of Microsoft 365 and desktop support.
• Experience with Active Directory, networking concepts, hardware repair, and troubleshooting.
• Excellent customer service, communication, and problem-solving skills.
• Ability to manage multiple priorities in a fast-paced environment.

Preferred

• Experience with SQL Server, Exchange, WSUS, Mimecast, and Datto.
• Experience supporting both onsite and remote users.

• Competitive compensation ( $26.00 - $32.00 hourly)
• Comprehensive health, dental, and vision benefits
• 401(k) with company match
• Paid holidays and generous PTO
• Stable and growing organization
• Collaborative team environment
• Opportunities for professional growth and development

EEO Employer – Veterans and IWD are strongly encouraged to apply

Labelmaster is proud to be an Equal Employment Opportunity Employer and we are committed to the concept and practice of equal opportunity in all aspects of employment. It is our intent to comply with our duty to provide reasonable accommodations for qualified employees and applicants as required by law. All requests for accommodations should be made in writing to Jay Hollins by emailing

Pay Transparency Policy Statement - The contractor will not discharge or in any other manner discriminate against employees or applicants because they have inquired about, discussed, or disclosed their own pay or the pay of another employee or applicant. However, employees who have access to the compensation information of other employees or applicants as a part of their essential job functions cannot disclose the pay of other employees or applicants to individuals who do not otherwise have access to compensation information, unless the disclosure is (a) in response to a formal complaint or charge (b) in furtherance of an investigation, proceeding, hearing, or action, including an investigation conducted by the employer, or (c) consistent with the contractor's legal duty to furnish information.