Technology Systems & Support Supervisor
School Health, Rolling Meadows, IL, United States
Technology Systems & Support Supervisor
On-Site | Rolling Meadows, IL
Full-Time | Exempt
About School Health
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 Role
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.
What You'll Do
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
What Success Looks Like
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
What We're Looking For
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
Compensation
Salary Range:
$62,006.50 - $96,015.48 annually
Classification:
Exempt (Salaried)
Benefits
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.
On-Site | Rolling Meadows, IL
Full-Time | Exempt
About School Health
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 Role
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.
What You'll Do
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
What Success Looks Like
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
What We're Looking For
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
Compensation
Salary Range:
$62,006.50 - $96,015.48 annually
Classification:
Exempt (Salaried)
Benefits
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.