Technology Systems & Support Supervisor

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.

• Design, configure, administer, and secure Windows Server environments. Physical and virtual (VMware/Hyper‑V/Azure)
• Manage network infrastructure including switches, routers, Sonic Wall firewalls, VLANs, VPNs, and wireless
• Administer Microsoft 365, Azure Active Directory/Entra , Intune MDM, Exchange Online, and Share Point
• Own backup and disaster recovery, 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

Salary Range: $62,006.50 – $96,015.48 annually

• 401(k) eligible
• Full benefits package (medical, dental, vision, and more)
• PTO and paid holidays

• 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