Bowman Williams · 1 week ago
Systems Administrator – MSP Escalations & Cloud Support
Rolling Meadows, IL
Full-time
Hybrid
Entry, Mid Level
$60K/yr - $85K/yr
2+ years expBowman Williams is a fast-growing Managed Service Provider (MSP) supporting small to mid-sized businesses throughout the Chicago suburbs. They are seeking a Systems Administrator to act as a technical escalation point, troubleshoot Microsoft ecosystem issues, and contribute to project work in a collaborative environment.
Office AdministrationRecruitingStaffing Agency
Hiring Manager
Robert Woodard
Responsibilities
Act as a true technical escalation point, owning complex issues from intake through resolution
Troubleshoot across the Microsoft ecosystem, including Microsoft 365, Azure Entra ID, identity, access, and endpoint-related issues
Administer and support Microsoft 365 environments, including Exchange Online, mail flow issues, shared mailboxes, permissions, and licensing
Diagnose login, MFA, and access problems involving Conditional Access, device trust, and endpoint compliance
Troubleshoot networking-related issues to identify root cause (endpoint vs network vs ISP vs Microsoft)
Support and validate backup and recovery systems, assisting with restores when needed
Document work thoroughly in ConnectWise PSA (or similar) with clean, professional ticket notes
Contribute to project work (deployments, migrations, rollouts), including occasional onsite client visits
Work collaboratively in a non-siloed MSP where everyone supports the queue and senior engineers help triage and guide
Qualification
Required
Previous experience working at a Managed Service Provider (MSP)
Strong troubleshooting skills across Microsoft 365, Azure Entra ID, Windows endpoints, and identity/access issues
Hands-on experience with Exchange Online, mail flow troubleshooting, permissions, and licensing
Working knowledge of Azure Entra ID, including users, groups, MFA issues, and Conditional Access basics
2+ years of experience with networking fundamentals (VLANs, switches, firewalls, routing concepts)
Experience supporting Windows Server or server-adjacent infrastructure
Familiarity with backups, endpoint security, VPN access issues
Ability to work independently, own problems, and escalate appropriately with context
Strong communication skills and comfort working directly with end users
Preferred
Intune (device enrollment, compliance, BitLocker, endpoint troubleshooting)
Meraki, SonicWall, or Ubiquiti environments
Prior experience in less-structured MSPs where autonomy is expected
Relevant certifications (not required, but a plus)
Benefits
Hybrid flexibility: Primarily remote with onsite client visits as needed (1–2x/week)
Unlimited PTO (trust-based; typically after ~6 months)
Medical: Blue Cross plans (HMO / PPO / HDHP w/ HSA), ~75% employer-paid
Dental & Vision: 100% employer-paid for employee
Culture perks: Social, team-oriented environment with real camaraderie
Growth runway: Exposure to escalations + projects with room to level up
Company
Bowman Williams
Bowman Williams is a staffing firm for IT managed and cloud service providers.
11-50 employees
Funding
Current Stage
Early StageLeadership Team
John Davenjay
CEO
Company data provided by crunchbase