IT Specialists MSP

We’re hiring an IT Specialist (Hybrid – Chicago Area) for a niche, highly respected MSP that exclusively supports senior living communities. This is not a churn-and-burn helpdesk. This is a white-glove, relationship-driven environment where professionalism, accountability, and trust matter just as much as technical skill.

You won’t just “work tickets.

You’ll be the visible, dependable face of IT for one of the most prestigious communities in Chicago and supporting additional high-end communities across the area.

This is a long-term career role. Many team members describe this company as their “retirement position.” That tells you everything about stability and culture.

• Support Wi‑Fi infrastructure (Ubiquiti), VLANs, switches, and Sonic Wall firewalls
• Document thoroughly in Connect Wise
• Act as the bridge between users and remote Tier 2/3 engineers
• Assist with light project work (Wi‑Fi refreshes, AP installs, infrastructure upgrades)
• Maintain proactive communication and professional client presence

• ~3 days onsite in Oak Park, IL

Base Salary:
Up to $75,000

• Medical
• Life, AD&D, Disability
• Hybrid flexibility with understanding leadership

• Prior MSP experience
• Strong Microsoft 365 stack knowledge
• Networking fundamentals (VLANs, Wi‑Fi, switches, firewalls)
• Ubiquiti and Sonic Wall exposure
• Professional, client‑facing communication