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.
On the infrastructure side, you'll own it end to end:
- 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
On the team leadership side, you'll be the person the helpdesk counts on:
- 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
And across both sides of the role:
- 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
Salary Range: $62,006.50 – $96,015.48 annually
Classification: Exempt (Salaried)
- 401(k) eligible
- Full benefits package (medical, dental, vision, and more)
- PTO and paid holidays
Work Location & Requirements
- 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
If you’re someone who takes ownership, sweats the details, and genuinely enjoys solving hard problems — while also getting satisfaction from helping a team do their best work — this role was built for you.