Entry Level Windows Server Jobs in Chicago, IL (NOW HIRING)

IT Support Specialist (Entry Level--On Site)

Are you looking to break into IT the right way?

Not by sitting in a narrow help desk role...

But by getting real, hands-on experience across internal IT support, Microsoft systems, networking, security, and business applications?

We are looking for someone who:

• Doesn't need to know everything, but knows how to figure things out
• Is comfortable researching, troubleshooting, and digging until the problem is solved
• Wants exposure to real-world IT systems, not just tickets and scripts
• Takes pride in being the person others rely on when something isn't working
• Understands that good IT support is a mix of technical skill, communication, patience, and follow-through

About Us

MNI is a long-established Evanston-based company (founded in 1912) that has evolved into a modern data and SaaS business. Our platforms, IndustrySelect and IndustryNet, are used by millions of professionals each year.

We are a small, privately owned company with approximately 90 employees and a highly collaborative environment. There is limited red tape and you will work directly with leadership, including the IT Director and CTO. This is a practical, hands-on environment where you will be exposed to many parts of IT and technology.

Our Environment

MNI is primarily a Microsoft-based organization with Windows 11 PCs, Microsoft Office/Microsoft 365, Windows servers, Active Directory, printers, VOIP phones, and SonicWall VPN access. You do not need to be an expert in all of these areas on day one, but you should be eager to learn them.

What You Will Be Doing

This is a hands-on, day-to-day IT support role for our internal team and systems. You will handle many front-line support needs while receiving direction, backup, and mentoring from the IT Director and CTO.

Core Responsibilities:

• Provide technical support to employees in person, by phone, and by email
• Set up, configure, and deploy Windows 11 PCs, laptops, monitors, and workstations
• Troubleshoot hardware, software, connectivity, VPN, printer, VOIP phone, and office equipment issues
• Assist with user accounts, permissions, passwords, email, and SonicWall VPN access
• Help with onboarding and offboarding tasks for employees
• Document issues, fixes, procedures, inventory, and recurring support patterns
• Escalate more complex issues appropriately while still following through to resolution
• Run daily invoicing and billing jobs

Additional Exposure (as you grow):

• Support Windows servers, Active Directory, file shares, security groups, and related systems
• Assist with internal systems, databases, websites, and business applications
• Participate in infrastructure, security, backup, patching, and disaster recovery processes
• Help evaluate and recommend hardware, software, vendors, and process improvements

What We Are Looking For

Required:

• Strong problem-solving ability and persistence
• Willingness to learn and research unfamiliar issues
• Attention to detail and follow-through
• Clear communication skills and good judgment when supporting employees
• Friendly, patient, and professional demeanor
• Ability to work independently while knowing when to ask for help
• Respect for confidentiality, security, and responsible handling of company systems and data

Helpful:

• Familiarity with Windows 11 environments
• Exposure to Microsoft Office/Microsoft 365, Active Directory, or basic Windows administration
• Exposure to networking concepts, VPNs, SonicWall, printers, or VOIP phones
• Basic knowledge of SQL, databases, websites, scripting, or automation
• Technical coursework, degree, certification, lab experience, or hands-on personal IT projects

Why This Role Is Different

Most entry-level IT roles are narrow and repetitive. This one is not.

• Work directly with the IT Director, CTO, and internal team
• Gain exposure to support, infrastructure, systems, security, and applications
• Learn by doing, not just following scripts
• Build a foundation for higher-level IT roles
• Make a visible difference in a smaller company where people know and appreciate good support

Position Details

Title: IT Support Specialist (Entry Level)

Location: Evanston, IL (On-site)

Schedule: Monday-Friday, 8:30 AM - 4:00 PM (35 hours/week)

Pay: $22-$24 per hour (based on experience)

Benefits:

• Paid holidays and vacation (PTO)
• Medical and dental insurance
• 401(k)
• Convenient location near Metra, CTA, and bus lines (parking available)

If you are looking to learn fast, gain real experience, and build a career in IT, we would like to learn more about you. Apply today (no phone calls, please)

MNI is a small, family-owned company that treats its employees like family. We offer a fun, laid-back environment with business casual dress attire. Our 80 employees work both in our Evanston office and remotely, and the owner is here and accessible every day. We are conveniently located close to both the CTA and Metra stations. There’s a reason why so many employees have been here for decades!