Technical IT Support Specialist - Chicago, IL

The Role

We are looking for a technically minded IT support professional who can bridge the gap between end-user helpdesk and senior engineering. You are not a traditional help desk — you understand systems well enough to triage a network issue, interpret a monitoring alert, and know whether to resolve it yourself or get the right engineer involved. You will own monitoring across our network, cloud, and NaaS environments, serve as the first-level escalation for technical issues, and support endpoint and device management operations. When something is wrong somewhere in our environment, you will often be the first to know.

What You'll Own

Monitoring & Observability

• Monitor network, cloud, and NaaS environments using observability and alerting platforms — Splunk, cloud monitoring consoles, and remote management tools

• Own NaaS site monitoring — track link health, power telemetry, and connectivity status for all active remote sites

• Respond to and triage monitoring alerts; resolve within your scope or escalate with full context to the appropriate engineer

• Manage NaaS firmware and configuration changes for live sites in coordination with the Field Engineering team

Technical First-Level Support

• Serve as the first technical escalation point for issues routed up from the helpdesk — network connectivity, application access, system performance

• Perform first-level network troubleshooting — diagnosing issues before escalating to the Senior Network Engineer

• Own the technical ticket queue for infrastructure-adjacent issues, ensuring nothing sits unrouted

• Contribute to SLA compliance by maintaining response time discipline and clear ticket documentation

Endpoint & Device Support

• Assist the Identity & Endpoint Systems Administrator with device enrollment (Intune, Apple Business Manager), compliance policy deployment, and device imaging

• Support OS patching cycles for Windows and Linux systems under direction of the Systems & Application Engineer

• Contribute to knowledge base and troubleshooting documentation for recurring issues

What We're Looking For

Required

• 3+ years in an IT support, NOC, or junior systems administration role

• Working knowledge of networking concepts — TCP/IP, DNS, VLANs, subnetting, basic firewall behavior

• Experience with monitoring and alerting platforms — Splunk, PRTG, Datadog, Zabbix, or equivalent

• Familiarity with Microsoft Intune or another MDM platform for device enrollment and policy deployment

• Experience supporting Windows environments at a systems level — not just end-user troubleshooting

• Strong communication skills — ability to escalate clearly, document concisely, and keep stakeholders informed during incidents

• Experience with a ticketing platform (Jira Service Management preferred)

Preferred

• Experience monitoring or supporting remote or field-deployed network infrastructure

• NaaS, managed connectivity, ISP, or telecom support background

• Splunk experience — dashboards, searches, alert configuration

• Basic scripting ability — PowerShell or Python for automation or log parsing

• Linux command-line proficiency at a support level

Details

• Location: Remote — must be available during core US business hours

• Travel: Minimal

• Employment type: Full-time