IT Support Specialist

R H Wine & Co Inc; St. Charles (IL); Hybrid; USD 75,000 - 90,000; Full time

Benefits offered by this job

20 days PTO

Paid holidays

Birthday off

Medical, dental, and vision insurance

Telemedicine

Parental Leave

Professional development support

LinkedIn Learning

Life Insurance

Short/Long-term disability

Job summary

IPMG (Insurance Program Managers Group) in St. Charles, IL is seeking an IT Support Specialist to deliver Level 1–2 technical support for employees and contractors. The role covers onboarding/offboarding, device deployment, and endpoint management, with a strong emphasis on documentation and customer service.

The position is hybrid, based in St. Charles with four days in the office for the first 90 days and three days later, 7:00 a.m.–4:00 p.m. ET.

Qualifications

• Five or more years of progressive IT support, help desk, desktop support, or equivalent hands-on technical experience.
• Working knowledge of computer hardware, Windows desktop operating systems, Microsoft 365 applications, and common troubleshooting practices.
• Ability to communicate clearly with technical and nontechnical users and provide professional, customer-focused support.
• Ability to organize work, document activities accurately, protect confidential information, and meet established timelines.
• Ability to work independently, recognize when escalation is needed, and collaborate effectively with other IT team members.

Responsibilities

• Provide Level 1 and Level 2 support by telephone, email, remote tools, and in person; document, track, prioritize, and monitor requests through timely resolution.
• Prepare, deploy, maintain, and troubleshoot laptops, desktops, mobile devices, printers, peripherals, and approved business applications.
• Perform employee and contractor onboarding and offboarding, including account setup, access changes, equipment preparation, and recovery of company assets.
• Assist with Microsoft 365, Windows, endpoint management, identity and access, collaboration tools, and common business application support.
• Maintain accurate hardware, software, licensing, and asset inventory records; support periodic software inventory reviews and governance activities.
• Support cybersecurity and compliance activities, including endpoint compliance, vulnerability remediation follow-up, access reviews, security documentation, and employee security support.
• Create and maintain technical documentation, user instructions, support procedures, and knowledge-base articles.
• Additional projects as assigned.

Skills

IT support

Help desk

Desktop support

Microsoft 365

Windows OS

Education

Associate or Bachelor's degree in IT or related field

Tools

Microsoft 365 administration

Entra ID

Intune

Ticketing systems

Remote support tools

Job description

If you are unable to complete this application due to a disability, contact this employer to ask for an accommodation or an alternative application process.

IT Support Specialist

St. Charles, IL, US

Salary Range: $75,000.00 To $90,000.00 Annually

Under the direction of the IT Support Manager, the IT Support Specialist provides responsive, customer-focused technical support to employees and contractors. The position supports onboarding and offboarding, account administration, workstation deployment, endpoint and software support, inventory management, vendor coordination, and issue documentation. The role is intended for an individual who can build technical knowledge and assume broader responsibilities as the organization grows.

This hybrid role is based out of our St. Charles, IL office, with four days in office for the first 90 days and three days thereafter. The schedule is 7:00 a.m.–4:00 p.m. to support our Eastern Time Zone business needs. The salary range is $75,000 - $90,000 annually. We typically target the midpoint of our range, and pay will be based on relevant experience.

What You'll Do

• Provide Level 1 and Level 2 support by telephone, email, remote tools, and in person; document, track, prioritize, and monitor requests through timely resolution.
• Prepare, deploy, maintain, and troubleshoot laptops, desktops, mobile devices, printers, peripherals, and approved business applications.
• Perform employee and contractor onboarding and offboarding, including account setup, access changes, equipment preparation, and recovery of company assets.
• Assist with Microsoft 365, Windows, endpoint management, identity and access, collaboration tools, and common business application support.
• Maintain accurate hardware, software, licensing, and asset inventory records; support periodic software inventory reviews and governance activities.
• Support cybersecurity and compliance activities, including endpoint compliance, vulnerability remediation follow-up, access reviews, security documentation, and employee security support.
• Create and maintain technical documentation, user instructions, support procedures, and knowledge-base articles.
• Additional projects as assinged.

Your Experience

• Five or more years of progressive IT support, help desk, desktop support, or equivalent hands-on technical experience.
• Working knowledge of computer hardware, Windows desktop operating systems, Microsoft 365 applications, and common troubleshooting practices.
• Ability to communicate clearly with technical and nontechnical users and provide professional, customer-focused support.
• Ability to organize work, document activities accurately, protect confidential information, and meet established timelines.
• Ability to work independently, recognize when escalation is needed, and collaborate effectively with other IT team members.

Preferred Qualifications

• Associate or bachelor’s degree in information technology, computer science, cybersecurity, or a related field, or equivalent experience.
• Experience with Microsoft 365 administration, Entra ID, Intune or other endpoint management platforms, ticketing systems, and remote support tools.
• Relevant entry-level or intermediate certification, such as CompTIA A+, Network+, Security+, or a Microsoft certification.
• Interest and demonstrated ability to grow into broader technical, operational, and future support leadership responsibilities.
• Flexible working hours, including Summer Fridays
• Generous Time off - 20 days of PTO, paid holidays, paid Birthday off
• Medical, dental, and vision coverage on day one of full-time employment, including telemedicine
• Paid Parental Leave for both Moms and Dads
• Professional development support and a Linkedin Learning subscription
• Life Insurance, Short term, and long-term disability on day one of full-time employment and paid for by IPMG

About IPMG

Insurance Program Managers Group (IPMG) is a growing insurance organization built on strong relationships, collaboration, and doing right by our clients and our people. We believe that from the front desk to the CEO’s office, everyone plays an equally important role in providing the highest level of service to our clients and independent agent and broker partners. We take great pride in our people and that pride is reflected every day in the commitment and effort given by our team.

Our hiring process is designed to be a two-way conversation. After your application is received, the process begins with a 20-minute phone conversation to get to learn about your experience, goals, and what you’re looking for next. If that goes well, the next step is a conversation with the hiring manager, and in some cases, other team members. Here you will dive deeper into the role, the team, and how you’d make an impact at IPMG.

Candidates that are selected and hired will need to submit to substance, credit, and criminal background screenings.

IPMG is an Equal Opportunity Employer—M/F/D