Technology Systems & Support Supervisor

On-Site | Rolling Meadows, IL

Full-Time | Exempt

School Health has specialized exclusively in the school market for more than 65 years, partnering with schools and districts nationwide to support student health, safety, and wellness. We're a trusted provider of products, programs, and expertise! Our Technology team is a core part of what keeps that mission running every day.

The Technology Systems & Support Supervisor owns the day-to-day operation and reliability of our server, network, and cloud infrastructure while directly leading a small helpdesk team. You'll be the person who can drop into a complex firewall issue in the morning and coach a team member through a tough support call in the afternoon. This is not a helpdesk manager role. And it's not a pure infrastructure engineer role. It's both! And that's exactly what makes it interesting.

You'll report to the Business Systems & IT Operations Manager and play a key role in shaping how technology runs and improves across the organization.

• Design, configure, administer, and secure Windows Server environments. Physical and virtual (VMware/Hyper-V/Azure)
• Manage network infrastructure including switches, routers, SonicWall firewalls, VLANs, VPNs, and wireless
• Administer Microsoft 365, Azure Active Directory/Entra ID, Intune MDM, Exchange Online, and SharePoint
• Own backup and disaster recovery, this is including: testing, documentation, and integrity reporting
• Plan and execute patching cycles and maintenance windows with minimal business disruption
• Maintain security posture across endpoints, firewall rules, access controls, and incident response

• Supervise, coach, and develop Helpdesk Analysts including performance feedback and career growth conversations
• Ensure the team consistently meets service level objectives and response targets
• Step in as the senior escalation point for complex or high-priority incidents that require your level of expertise
• Keep IT Operations Manager informed of recurring issues, risk areas, and improvement opportunities

• Build and maintain technical documentation including: runbooks, topologies, SOPs, and training materials
• Identify and recommend technology solutions that align with business strategy
• Participate in infrastructure and process improvement projects
• Assist with budget planning, vendor renewals, and software licensing

• Infrastructure runs reliably & secure. Issues are caught early, patching is current, and backups are verified
• The helpdesk team is supported, growing, and consistently hitting service level targets
• Complex problems get solved - not just escalated or worked around
• Documentation exists and stays accurate - the next person can pick up where you left off
• You're a trusted partner to both your team and the broader business — not just a ticket resolver

• 5–7 years of progressive IT experience, with at least 2 years in a supervisory or team lead capacity
• Hands-on expertise in Windows Server, networking fundamentals, and Microsoft 365/Azure administration
• Comfortable owning infrastructure and leading people
• Strong troubleshooting instincts and comfort working through problems where the answer isn't obvious
• Clear, direct communicator who can translate technical issues for non-technical stakeholders
• Detail-oriented and thorough, you follow through and verify your work
• Bachelor's degree in Information Technology, Computer Science, or a related field; equivalent experience considered
• ITIL Foundations certification recommended

• On-site role based in Rolling Meadows, IL
• Occasional after-hours maintenance windows are part of the job
• Must be able to lift and carry up to 50 lbs