System Administrator Level 2.; MSP

Senior Business Operations Manager & Cloud Recruiter at Bowman Williams

We are an MSP supporting small and mid sized businesses across the Chicagoland area. Our team offers the pace and variety of a local MSP with the support and structure of a larger organization. We value ownership, consistency, and continuous learning, and we are looking for a System Administrator with MSP experience who wants to grow while taking on meaningful technical responsibility.

This role is a strong fit for a mid level MSP engineer who can handle escalations, keep server environments healthy, and contribute to Microsoft 365 and Azure projects. You will work across multiple client networks, support cloud migrations, and partner with senior engineers on upgrades and modernization work.

• Take ownership of escalations across Windows Server, Microsoft 365, Azure, and core networking
• Administer Windows Server 2016 to 2022 including Active Directory and Group Policy
• Support Microsoft 365 migrations and improvements including Exchange Online and One Drive
• Work with Azure services including Entra , Intune, and Azure Virtual Desktop
• Troubleshoot DNS, DHCP, VPN connectivity, VLANs, and firewall related issues
• Assist with infrastructure upgrades, refreshes, and cloud transition projects
• Maintain clean documentation and ticket updates in PSA and RMM tools
• Travel to client sites as needed for deployments, maintenance, and higher touch support

• 3 to 5 years of MSP experience supporting multiple client environments
• Strong skills in Microsoft 365, Azure, and Windows Server 2016 to 2022
• Solid networking fundamentals including DNS, DHCP, VLANs, VPNs, and firewalls
• Experience supporting Entra , Intune, and Azure Virtual Desktop
• Comfortable handling escalations and participating in project work
• Familiarity with Autotask and Kaseya or similar MSP toolsets
• Strong communication, documentation, and problem solving skills
• Certifications like Network+ or Microsoft 365 or Azure are a plus

• Chicagoland area role with client site visits as needed
• Hybrid schedule after onboarding, 2 to 3 days work from home
• Salary up to $90K plus monthly performance bonus
• Health, dental, and vision insurance
• Mileage reimbursement for client visits
• Training and certification reimbursement
• Supportive MSP culture with clear growth path

• Mid-Senior level

• Full-time

• Information Technology

• IT Services and IT Consulting

• Medical insurance
• Vision insurance
• 401(k)
• Disability insurance
• Paid paternity leave
• Paid maternity leave

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