System Engineer L2.5

3 weeks ago

Chicago, United States Bowman Williams Full time

System Engineer (Level 2.5) – Hybrid | Chicago-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: Windows Server 2016–2022, Active Directory, GPO SonicWall, Meraki, Unifi, VLANs, VPNs VMware & Hyper‑V & Azure VMs (installations, migrations, management) RMM/PSA: ConnectWise, N‑Able, Datto, or similar Cyber Security Why You’ll Love It Here: Career Track to Senior Engineer or vCIO — we promote from within and tailor growth plans True Project Exposure — not just maintenance; real‑world deployments weekly Client Variety = Constant Learning — industries include law, healthcare, finance, creative, and more Mentorship Culture — learn directly from experienced Tier 3s and senior architects Flexible Hybrid Setup — be onsite for big impact, remote for deep focus Autonomy + Support — own your work, but never alone You Might Be a Fit If You: Have 2–6 years of MSP experience Have project 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 401(k) with company match PTO + Paid Holidays Tight-knit, high-skill team culture where people actually support each other Must have MSP Experience #J-18808-Ljbffr

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    1 week ago

    Chicago, Illinois, United States Bowman Williams Full time $80,000 - $95,000 per year

    System Engineer (Level 2.5) – Hybrid | Chicagoland-Based MSPLocation:Chicago, IL|Schedule:Hybrid (2–3 days onsite/week)Salary:Competitive ($80K–$95K) + Benefits + Bonus + Fast-Track to Senior EngineeringAre 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...

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    2 weeks ago

    Chicago, United States Bowman Williams Full time

    System Engineer (Level 2.5) – Hybrid | Chicagoland-Based MSPLocation: Chicago, IL| Schedule: Hybrid (2–3 days onsite/week)Salary: Competitive ($80K–$95K) + Benefits + Bonus + Fast-Track to Senior EngineeringAre 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...

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    2 weeks ago

    Chicago, United States Bowman Williams Full time

    System Engineer (Level 2.5) – Hybrid | Chicagoland-Based MSPLocation: Chicago, IL| Schedule: Hybrid (2–3 days onsite/week)Salary: Competitive ($80K–$95K) + Benefits + Bonus + Fast-Track to Senior EngineeringAre 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...

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