Hybrid IT & AI Systems Manager

Usagain, Llc; Chicago (IL); Hybrid; USD 100,000 - 120,000; Full time

Benefits offered by this job

Medical: 80% Company Paid

Dental & Vision Coverage

Short-Term Disability

Long-Term Disability

401(k) Program

Life & Accidental Death Insurance

9 Paid Holidays

Safety Bucks Program

Wellness Programs

Job summary

USAgain is hiring an Information Systems Manager to lead our IT support team and ensure seamless operation of technology and business applications. The role covers end‑user support, Microsoft 365 administration, email security, device management, and AI tool adoption to boost productivity across teams.

You’ll manage a team responsible for hardware and software support, maintain system security, and partner with vendors to keep operations running smoothly in a hybrid West Chicago, IL environment.

Qualifications

• 6+ years in IT or IS support, including 3+ years leading a team.
• Hands-on Microsoft 365 administration experience (Exchange Online, Entra ID, Teams).
• Working knowledge of networking, email security, MFA, and endpoint protection.
• Experience supporting business applications and working with software vendors.
• Experience with server administration including cPanel/WHM/SSH, web hosting, and MySQL database administration.
• Familiarity with APIs, PHP, and MySQL database querying.
• Strong troubleshooting skills across Windows, macOS, and mobile devices.
• Clear communicator who can explain technical issues to non-technical staff.

Responsibilities

• Lead, schedule, and develop the hardware and software support team.
• Coordinate with internet service providers and network vendors.
• Manage email security, including spam and phishing filtering.
• Set priorities, manage the ticket queue, and track response and resolution times.
• Serve as the escalation point for complex or high-impact issues.
• Document procedures and build a knowledge base for staff and end users.
• Oversee help desk support for computers, peripherals, phones, and network connectivity.
• Support the business applications our operations rely on, including CRM/ERP custom system and integrations with company mobile Apps and payroll system.
• Evaluate and recommend AI tools, such as Microsoft 365 Copilot, that improve productivity across teams.
• Lead rollout, configuration, and licensing of approved AI tools.
• Set and enforce policies for safe AI use, including data protection, privacy, and access controls.
• Train staff on effective and responsible use of AI tools.
• Identify opportunities to automate routine support and operations tasks with AI.

Skills

IT support

Team leadership

Microsoft 365 administration

Networking

Email security

Problem solving

Communication

Education

Bachelor’s degree in Information Systems/Computer Science

Tools

Exchange Online

Entra ID

Teams

cPanel/WHM/SSH

MySQL

PHP

APIs

SugarCRM/SuiteCRM

Job description

USAgain is hiring an Information Systems Manager to lead our IT support team and ensure seamless operation of technology and business applications. The role covers end‑user support, Microsoft 365 administration, email security, device management, and AI tool adoption to boost productivity across teams.

You’ll manage a team responsible for hardware and software support, maintain system security, and partner with vendors to keep operations running smoothly in a hybrid West Chicago, IL environment.