IT Support Specialist - II

Windstar Technologies, Inc. provides technology support to business clients across multiple locations and industries. As an IT Support Specialist II, you will resolve escalated technical issues, support users remotely and at client offices, and help maintain reliable, secure client systems.

You will own assigned support requests, explain issues clearly, and escalate complex infrastructure issues and changes to senior engineers. This role combines hands-on troubleshooting with direct customer service.

What you will do:

• Resolve Level 2 support requests involving Windows workstations, business applications, printers, peripherals, and connectivity, including escalations from Level 1 technicians. Support clients by phone, remotely, and at their offices.

• Support Microsoft 365 accounts, licensing, email, and applications within your assigned administrative permissions.

• Perform routine Active Directory and Windows Server administration and troubleshooting, including user and computer accounts, groups, permissions, Group Policy, DNS, and DHCP.

• Diagnose network issues involving Meraki firewalls, switches, wireless connectivity, routing, and VPNs. Perform approved changes and escalate complex infrastructure problems.

• Use RMM for remote support, endpoint monitoring, patching, and approved maintenance.

• Monitor Backup jobs, troubleshoot failures, and assist with approved recovery procedures and restore verification.

• Review and triage alerts from AV/EDR and security tools. Follow documented response procedures and escalate suspected incidents to the appropriate team.

• Install and configure workstations, software, and peripherals; assist with onboarding and offboarding; and maintain equipment and software license records.

• Manage assigned tickets by business impact, urgency, and service commitments. Keep clients informed and document diagnostic steps, work performed, time, and resolution or handoff details.

• Protect client information, verify identity before account recovery, and follow access and change procedures. Maintain useful documentation, share solutions with Level 1 technicians, and assist engineers with client projects and equipment installations.

At least three years of relevant professional IT support experience, including direct support of business users.

• Demonstrated ability to independently troubleshoot Windows 11 workstations, common business applications, printers, and peripherals.

• Hands-on experience supporting Microsoft 365 and administering Active Directory users, groups, and permissions.

• Practical experience troubleshooting Windows Server services and network issues involving TCP/IP, DNS, DHCP, and VPN connectivity.

• Experience using a ticketing system and remote support or monitoring tools to manage competing requests, document troubleshooting, and make effective escalations.

• Clear written and verbal communication, strong customer service, reliable follow-through, and sound judgment when handling client access and information.

• Ability to work in person in Culpeper, travel to client offices as needed, and participate in the stated on-call rotation.

Preferred qualifications:

• Experience working for a managed service provider or supporting multiple business clients.

• Experience with RMM, Ticketing Systems, firewalls, Backups, or security products.

• Familiarity with Microsoft Entra ID, hybrid identity, endpoint management, or PowerShell for routine support tasks.

• Relevant certifications, including CompTIA A+, Network+, or Security+; Microsoft 365 Certified: Copilot and Agent Administration Fundamentals (AB-900); or Microsoft Certified: Azure Fundamentals (AZ-900). Certifications are preferred; demonstrated hands-on support skills are required.

• An associate or bachelor degree in IT or a related field, or equivalent technical training and practical experience.

Travel and physical requirements

This role includes travel to client offices. A valid driver’s license and reliable transportation are required. Essential duties include occasionally lifting or moving equipment weighing up to 50 pounds, such as servers, UPS units, and printers, with or without reasonable accommodation., * relevant professional IT support : 3 years (Preferred)

• Dental insurance
• Health insurance
• Paid time off
• Vision insurance