System Engineer (Level 2.5) Hybrid | Chicagoland-Based MSP
Location : Chicago, IL| Schedule : Hybrid (23 days onsite / week)
Salary : Competitive ($80K$95K) + Benefits + Bonus + Fast-Track to Senior Engineering
Are you stuck in a role where youve outgrown the tickets but havent 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?
Were a fast-moving MSP in the heart of Chicago looking for a sharp, well-rounded System Engineer (Tier 2.5) whos ready to dive deeper someone whos 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 whos almost there technically and looking for a team that will give you room to grow.
What Youll 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 cant, 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 Youll Touch :
Windows Server 20162022, Active Directory, GPOAzure AD, Intune, Exchange Online, M365SonicWall, Meraki, Unifi, VLANs, VPNsVMware & Hyper-V & Azure VMs (installations, migrations, management)RMM / PSA : ConnectWise, N-Able, Datto, or similarBackup & DR : Datto, Veeam, Acronis, etc.Cyber SecurityWhy Youll Love It Here :
Career Track to Senior Engineer or vCIO we promote from within and tailor growth plansTrue Project Exposure not just maintenance; real-world deployments weeklyClient Variety = Constant Learning industries include law, healthcare, finance, creative, and moreMentorship Culture learn directly from experienced Tier 3s and senior architectsFlexible Hybrid Setup be onsite for big impact, remote for deep focusAutonomy + Support own your work, but never aloneYou Might Be a Fit If You :
Have 26 years of MSPHave project experience with servers, firewalls, cloud migrations, and networkingAre confident working directly with clients, managing expectations, and communicating clearlyCan juggle priorities, keep documentation sharp, and act as a technical lead when neededThrive in dynamic, high-accountability environments with room to growCompensation & Perks :
$80K$95K base depending on experienceHealth, Dental, Vision Insurance401(k) with company matchPTO + Paid HolidaysProfessional development / certification reimbursementTight-knit, high-skill team culture where people actually support each otherMust have MSP Experience!!!