Tier 3 Help Desk Specialist

Post Date

Feb 23, 2026

Location

Chicago,
Illinois

ZIP/Postal Code

60601
US
Apr 25, 2026 Insight Global

Job Type

Contract,Perm Possible

Category

Help Desk

Req #

DGW-0dc5eea3-9903-44ab-b967-79966e9ac27e

Pay Rate

$41 - $51 (hourly estimate)

Job Description

Our real estate development client is seeking a strong Tier 3 Helpdesk Specialist to join their growing team in Chicago, IL. The environment consists of about 2,000 endpoints, workstations and laptops in a Windows server and OS environment. The Specialist will perform server and networking troubleshooting, handling escalations from Tier 1/2 and creating SOP documentation for future reference. Candidates should have senior, generalist user support experience and be willing to mentor junior technicians. We can offer $100-120K ($48-60/HR) for this position depending on experience.

We are a company committed to creating diverse and inclusive environments where people can bring their full, authentic selves to work every day. We are an equal opportunity/affirmative action employer that believes everyone matters. Qualified candidates will receive consideration for employment regardless of their race, color, ethnicity, religion, sex (including pregnancy), sexual orientation, gender identity and expression, marital status, national origin, ancestry, genetic factors, age, disability, protected veteran status, military or uniformed service member status, or any other status or characteristic protected by applicable laws, regulations, and ordinances. If you need assistance and/or a reasonable accommodation due to a disability during the application or recruiting process, please send a request to HR@insightglobal.com.To learn more about how we collect, keep, and process your private information, please review Insight Global's Workforce Privacy Policy: https://insightglobal.com/workforce-privacy-policy/.

Required Skills & Experience

- 5 years of IT user support experience
- Strong troubleshooting skills across Microsoft-centric environments:
• Windows Server administration, Active Directory / Entra ID concepts
• Microsoft 365 administration (Exchange Online, SharePoint/Teams fundamentals)
- Solid networking fundamentals (TCP/IP, DNS/DHCP, VPN, VLANs, firewall concepts).
- Experience with virtualization (VMware or Hyper-V) and backup/DR concepts.
- Strong written communication and client-facing professionalism.

Nice to Have Skills & Experience

- Experience supporting a MSP

Benefit packages for this role will start on the 1st day of employment and include medical, dental, and vision insurance, as well as HSA, FSA, and DCFSA account options, and 401k retirement account access with employer matching. Employees in this role are also entitled to paid sick leave and/or other paid time off as provided by applicable law.