IT Specialist/AI Tech

Connection has a fantastic opportunity through our Technical Staffing division for an IT Specialist supporting our client in Downers Grove, IL. This is an excellent opportunity to join a growing organization offering competitive contractor benefits with the potential to convert to a full-time employee. Once hired permanently, employees receive an excellent benefits package including 3 weeks of paid PTO, tuition reimbursement, 401(k), comprehensive medical, dental, and vision coverage, and outstanding career growth opportunities.

This is an onsite position located in Downers Grove, IL (60515) working Monday through Friday, 8:00 AM – 5:00 PM. There is no travel required.

What We Do

We calm the confusion of IT by guiding the connection between people and technology. If a customer is looking for a better way to manage their warehouse inventory, equip their workforce, or secure their data, we make it happen. All it takes is finding the right combination of tech hardware, software, cloud solutions, and support services. That’s what we do. We’re the IT Department’s IT Department.

Who We Are

Our team is made stronger by a multitude of backgrounds, experiences, and perspectives. It’s what makes Connection unique—what drives us to innovate and create technology solutions that stand apart from the crowd. We’d love for you to be a part of that fabric, to share your ideas and experiences with a team that thrives on fresh thinking, creativity, and helping others.

Why You Should Join Us

You’ll find supportive teammates and a rewarding career at Connection—plus great benefits. We take pride in supporting employees with a total rewards package that provides financial, emotional, and physical resources for you and your family.  Our compensation, 401k plans, medical insurance, and other benefits are progressive and competitive.  We value the importance of our employees’ emotional wellbeing. To support employees, we provide free therapy visits, mental health coaching and tools, and meditation resources. You’ll also enjoy a generous paid time off package that includes not only vacation and sick time, but also Wellness and Volunteer Time Off days. 

Applicants must be authorized to work for any employer in the U.S. We are unable to sponsor or take over sponsorship of an employment visa at this time.

We are seeking an IT Specialist who has a solid foundation in desktop support and a genuine interest in expanding their knowledge of Artificial Intelligence technologies. This is an exciting opportunity for someone who enjoys traditional IT support while also wanting hands-on exposure to emerging AI tools and initiatives.

Initially, the role will consist of approximately:

• 60% Desktop Support & IT Operations
• 40% AI Projects & Innovation

This position is ideal for someone who is naturally curious about AI and wants to grow into a more AI-focused role over time.

AI Responsibilities (Approximately 40%)

• Utilize and explore AI platforms such as Microsoft Copilot, ChatGPT, Gemini, or similar generative AI tools.
• Assist with AI initiatives and process improvements across the organization.
• Help develop, configure, or test AI agents or AI-powered workflows.
• Support experimentation with AI chatbots, automation, AI-generated content, and related technologies.
• Stay current on emerging AI trends and recommend new opportunities for improving business processes.
• Collaborate with internal teams to identify practical AI use cases.

IT Support Responsibilities (Approximately 60%)

• Provide desktop and end-user support by resolving service desk tickets.
• Configure and deploy desktop and laptop computers.
• Create, modify, and maintain Active Directory user accounts and permissions.
• Support Microsoft 365 / Office 365 users.
• Troubleshoot desktop hardware, software, printers, and peripheral devices.
• Perform PC inventory management, asset tracking, shipping, and receiving of equipment.
• Follow documented procedures while managing multiple priorities.
• Assist with general desktop support projects as needed.
• Maintain excellent customer service and communication with end users.

Qualifications

• 3+ years of IT support, desktop support, or help desk experience.
• Experience supporting Active Directory and Microsoft 365 / Office 365 environments.
• Strong troubleshooting and customer service skills.
• Excellent verbal and written communication abilities.
• Ability to multitask and follow established processes.
• Interest in learning and growing within Artificial Intelligence technologies.
• Experience using AI tools such as Copilot, ChatGPT, Gemini, or similar platforms.
• Exposure to AI agents, chatbots, prompt engineering, or AI automation is highly preferred.
• Self-motivated with a willingness to learn new technologies.

Physical Requirements

• Ability to bend, lift, carry, and move equipment weighing up to 30 pounds.
• Ability to transport computers and equipment using carts when necessary.

Preferred Qualifications

• Experience creating or experimenting with AI agents or AI workflows.
• Familiarity with AI image generation, AI bots, or business automation tools.
• Previous experience working in a Windows desktop support environment.

Because of the possibility for fraudulent job postings on many popular job boards, please be advised that Connection will never offer a position of employment without a complete interview process and communication with a “live person".