System Administrator L2 (MSP) Chicagoland Hybrid
Growth Track: Senior Engineer → Project Lead → Client Advisor
If you’ve worked in the SMB MSP world, you know the difference between a shop that “runs tickets” and one that builds careers. That’s the core of who we are.
We serve small–mid sized organizations that value responsiveness, clarity, and relationships — not enterprise red tape. We won #1 Best Workplace in Illinois because we built a place where engineers feel supported, mentored, and part of a team that wins together.
We’ve scaled rapidly over the last two years and are continuing to invest heavily in people, tooling, learning paths, and quality-of-life. This role was created to develop the next wave of our technical leaders.
Why this role exists
- Client growth = internal growth
- Internal career track needs new rising talent
- Clear skill ladder set by senior engineering, not “learn and drown”
If you want to continue growing technically without losing balance, sanity, or mentorship, this will feel like your place.
What You’ll Actually Do
- Own resolutions end-to-end, not just pass them along
- Strengthen Microsoft 365 environments (Teams, Exchange, SharePoint, Entra ID)
- Troubleshoot workstation, authentication, access, and connectivity issues
- Manage laptop/desktop setups, identity permissions, and basic networking fixes
- Collaborate with engineers who explain AND teach
- Participate in a coaching-oriented queue and no silos, no ego walls
This role is technical, but also relational — we expect clarity, calm communication, and follow-through.
What You Bring
- Comfort resolving Windows & M365 issues without handholding
- Experience in an MSP / IT services model (preferred but not required if you “get SMB”)
- Working knowledge of Teams, mailbox moves, access/permissions, SharePoint
- Basic networking comfort (Wi-Fi, VLANs, printers, switching concepts)
- Curiosity & hunger to progress into project work / senior engineering
Compensation & Perks
- $70K–$85K
- 3 weeks PTO
- Profit sharing
- Medical, dental, vision, telemedicine
- Life & disability coverage
- Weekly DoorDash meal benefit
- Certification bonuses & paid learning paths
- Recognition & rewards platform (earn PTO + bonuses)
- Retirement plan with company match
- True mentorship, not “sink or swim”
Why People Stay Here
- Coaching > pressure
- Growth > grind
- Quality-of-life > churn
- You’ll have upward mobility as we continue to scale into project engineering, senior technical work, and eventually client advisory if that fits your path.
