Bowman Williams
This range is provided by Bowman Williams. Your actual pay will be based on your skills and experience — talk with your recruiter to learn more.
Base pay range $70,000.00/yr - $85,000.00/yr
Direct message the job poster from Bowman Williams
Cloud Recruiter @ Bowman Williams | Thought Leader in MSP hiring System Administrator L2 (MSP) Chicagoland Hybrid
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
$70K–$85K
Profit sharing
Life & disability coverage
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.
Seniority level Mid‑Senior level
Employment type Full‑time
Job function Information Technology
Industries IT Services and IT Consulting and Information Services
Benefits
Medical insurance
Vision insurance
401(k)
Disability insurance
Paid paternity leave
Paid maternity leave
Life & disability coverage
Profit sharing
Recognition & rewards platform (earn PTO + bonuses)
Retirement plan with company match
Certification bonuses & paid learning paths
True mentorship, not “sink or swim”
Get notified about new System Administrator jobs in
Chicago, IL .
#J-18808-Ljbffr
Base pay range $70,000.00/yr - $85,000.00/yr
Direct message the job poster from Bowman Williams
Cloud Recruiter @ Bowman Williams | Thought Leader in MSP hiring System Administrator L2 (MSP) Chicagoland Hybrid
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
$70K–$85K
Profit sharing
Life & disability coverage
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.
Seniority level Mid‑Senior level
Employment type Full‑time
Job function Information Technology
Industries IT Services and IT Consulting and Information Services
Benefits
Medical insurance
Vision insurance
401(k)
Disability insurance
Paid paternity leave
Paid maternity leave
Life & disability coverage
Profit sharing
Recognition & rewards platform (earn PTO + bonuses)
Retirement plan with company match
Certification bonuses & paid learning paths
True mentorship, not “sink or swim”
Get notified about new System Administrator jobs in
Chicago, IL .
#J-18808-Ljbffr