Hybrid IT Support Specialist Level 2 — Windows & M365

Top Prospect Group; Millbury (MA); Hybrid; USD 34,000 - 41,000; Full time

Benefits offered by this job

Mileage reimbursement

Job summary

Top Prospect Group seeks a Level 2 IT Support Specialist to resolve escalated tickets, troubleshoot infrastructure, and partner with senior engineers on technology projects. The role offers hybrid work, a temp-to-perm path within 6 months, and opportunities to build hands-on experience with Windows, AD, O365, and networking.

The ideal candidate will handle server, workstation, and Microsoft 365 tasks while supporting client environments and maintaining documentation.

Qualifications

• 3+ years of experience in IT support or systems administration.
• Strong Windows troubleshooting with AD and MS 365 experience.
• Networking knowledge including DNS, DHCP, VLANs, VPNs, and firewalls.
• Experience with servers, backups, patching, and endpoint security.
• Excellent communication skills and a customer-focused approach.
• Valid driver’s license and willingness to travel to client sites.

Responsibilities

• Resolve escalated issues involving Windows Server, Active Directory, Microsoft 365, networking, and endpoint security.
• Troubleshoot DNS, DHCP, Group Policy, permissions, VPNs, and other infrastructure issues.
• Support Microsoft 365 administration, backups, patching, and monitoring.
• Handle complex workstation, imaging, application, and hardware issues.
• Assist with server upgrades, Microsoft 365 migrations, network refreshes, and onsite equipment replacements.
• Provide technical guidance to Tier 1 technicians and maintain accurate documentation.
• Participate in an after-hours on-call rotation.

Skills

Windows troubleshooting

Active Directory

Microsoft 365

Networking

Endpoint security

Documentation

Customer-focused communication

Job description

Top Prospect Group seeks a Level 2 IT Support Specialist to resolve escalated tickets, troubleshoot infrastructure, and partner with senior engineers on technology projects. The role offers hybrid work, a temp-to-perm path within 6 months, and opportunities to build hands-on experience with Windows, AD, O365, and networking.

The ideal candidate will handle server, workstation, and Microsoft 365 tasks while supporting client environments and maintaining documentation.