About the Opportunity:
A fast-growing boutique MSP in Crystal Lake is expanding—and looking for a skilled IT Support Specialist to join the team. This is more than a help desk role—it’s a chance to take ownership of escalated issues, shape service delivery, and carve out a path toward leadership. You’ll work directly with clients (primarily in the manufacturing space), support internal team members, and help improve how IT support is delivered company-wide.

This role is perfect for someone with deep troubleshooting experience, strong communication skills, and a proactive, process-driven mindset.

What You’ll Be Doing:

  • Serve as the escalation point for Tier 1 help desk—complex issues come to you
  • Own and manage the ticket queue, driving resolution and customer satisfaction
  • Troubleshoot and resolve issues involving Windows Server, M365, networking, and EDR/security platforms
  • Lead IT deployments and installations for new manufacturing clients
  • Maintain clean, consistent documentation and time entries
  • Contribute to process improvements that scale support and reduce recurring issues
  • Support and mentor junior team members

What You Bring to the Table:

  • Must have experience with Kaseya (RMM & ticketing)
  • Strong L2/L3 troubleshooting experience with:
  • Windows Server 2012+
  • Microsoft 365, Intune, Entra ID
  • VMware (ESXi, VCenter, VSphere)
  • WatchGuard firewalls
  • Datto RMM & EDR tools
  • Comfortable taking ownership of issues and driving them to resolution
  • Proactive, solutions-oriented mindset—constantly looking for ways to improve support
  • Strong documentation habits and time management skills
  • A team player who values integrity and transparency

Benefits & Perks:

  • 80% company-paid Medical & Vision insurance
  • Paid training & certification reimbursement (after passing)
  • 401(k) with employer match
  • Generous PTO policy and flex-time for after-hours work
  • Cell phone & internet stipend
  • Mileage reimbursement
  • Company-issued laptop
  • Stocked kitchen and branded gear
  • Regular employee performance reviews and growth plans
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