Job Description
System Engineer (Level 2) – Hybrid | Chicagoland-Based MSP
Location: Chicago, IL| Schedule: Hybrid (2–3 days onsite/week)
Salary: Competitive ($65K–$80K) + 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) 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:
- Windows Server 2016–2022, Active Directory, GPO
- Azure AD, Intune, Exchange Online, M365
- SonicWall, Meraki, Unifi, VLANs, VPNs
- VMware & Hyper-V & Azure VMs (installations, migrations, management)
- RMM/PSA: ConnectWise, N-Able, Datto, or similar
- Backup & DR: Datto, Veeam, Acronis, etc.
- Cyber Security
- You Might Be a Fit If You:
- Have 2–6 years of MSP
- Have administrative experience with servers, firewalls, cloud migrations, and networking
- Are confident working directly with clients, managing expectations, and communicating clearly
- Can juggle priorities, keep documentation sharp, and act as a technical lead when needed
- Thrive in dynamic, high-accountability environments with room to grow
- Compensation & Perks:
- $60K–$80K base depending on experience
- Health, Dental, Vision Insurance
- 401(k) with company match
- PTO + Paid Holidays
- Professional development/certification reimbursement
- Tight-knit, high-skill team culture where people actually support each other
Must have MSP Experience!!!
Apply Now
Apply Now