System Engineer L2.5 (MSP)
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
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