Tier 2.5 Systems Administrator (MSP)

Bowman Williams • Chicago, IL, US • $80k - $95k / year • 3w ago

Tier 2.5 Systems Administrator (MSP) - Hybrid | Des Plaines, IL

We’re a modern, growth-minded MSP led by a dynamic team that blends a fresh, energetic culture with battle-tested processes. You’ll join a tight-knit group of engineers who focus on mid-to-advanced work, not endless password resets. Expect real projects, modern tooling, and clients who value tech (with a strong footprint in architecture/engineering/construction). If you want your ideas to matter and your skills to accelerate, this is your next step.

Why you’ll love it

Hybrid schedule: ~3 days/week on-site in Des Plaines or at client offices after ramp; the rest remote
Career growth: clear paths, mentorship, and hands-on projects with the latest tech
Great environment: collaborative, low-ego, fun team that actually shares knowledge
Meaningful work: tackle complex problems, not ticket churn

What you’ll do

Resolve escalated issues via phone, remote, and on-site support for diverse SMB clients
Own Tier-2+ troubleshooting across servers, workstations, networking, and M365
Deploy and migrate endpoints (including seamless data moves to SharePoint/OneDrive)
Configure/maintain Intune, MFA, Conditional Access, GPOs, DNS/DHCP
Support firewalls and site-to-site VPNs; keep backups healthy and recoverable
Document thoroughly and communicate clearly with both clients and teammates
Participate in a light on-call rotation as needed

What Makes You a Great Fit

5+ years of hands-on IT experience, including significant Microsoft server/workstation work
Strong Intune administration; MFA & Conditional Access expertise
Confident with Active Directory/GPO, DNS/DHCP, and M365/SharePoint migrations
Comfortable with firewalls and site-to-site VPN setup/troubleshooting
Prior MSP experience (you know the pace and love the variety)
Excellent customer communication; calm under pressure; detail-driven

Nice to have