System Engineer L2.5 (MSP)

System Engineer (Level 2.5) – Hybrid | Chicagoland-Based MSP

Location : Chicago, IL| Schedule : Hybrid (2–3 days onsite / week)

Salary : Competitive ($80K–$95K) + Benefits + Bonus + Fast-Track to Senior Engineering

Are you stuck in a role where you’ve outgrown the tickets but haven’t been given the reins? Ready to take on complex environments, manage deployments end-to-end, and step into senior-level responsibilities with support and mentorship behind you?

We’re a fast-moving MSP in the heart of Chicago looking for a sharp, well-rounded System Engineer (Tier 2.5) who’s ready to dive deeper — someone who’s not just familiar with projects and escalations, but thrives in client-facing environments, works autonomously, and wants to carve a real career path in infrastructure, cloud, or leadership.

This is the role for someone who’s “almost there” technically and looking for a team that will give you room to grow.

What You’ll Be Doing :

• Project Ownership : Deploy servers, configure and manage firewalls, run migrations (M365, Intune, AD, etc.), and lead small-to-medium client infrastructure projects from kickoff to close
• Advanced Support & Escalations : Be the escalation point for Tier 1s / 2s — solving the tough issues they can’t, owning tickets end-to-end
• Cloud & Hybrid Infrastructure : Manage Azure AD, Exchange Online, Intune, and Office 365 environments across a variety of SMB clients
• Security & Network Config : Build VLANs, manage SonicWall / Meraki / Ubiquiti environments, implement VPNs, and ensure endpoint protection
• Mentorship & Process : Help shape SOPs and best practices — mentor junior staff and help improve delivery standards
• Client Relationships : Be a trusted face with our clients — present solutions clearly, own issues, and provide guidance that builds trust

Tech You’ll Touch :

Why You’ll Love It Here :

You Might Be a Fit If You :

Compensation & Perks :

Must have MSP Experience!!!