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 tot his job Apply To this Job