Senior IT Support Engineer (Tier 2/3)

I.T. WORKS! Inc. is hiring a Senior IT Support Engineer (Tier 2/3) for an on-site role in West Barnstable, MA. This position supports clients with hands-on troubleshooting, escalated ticket ownership, and technical work across Windows, Microsoft platforms, networking, and infrastructure.

Role Overview

As a Senior Tier 2/3 IT Support Engineer, you will resolve advanced support issues beyond the frontline Support Team, collaborate with engineers on difficult cases, and assist with infrastructure and project work. The role includes participation in an on-call rotation (including occasional weekends) and occasional travel to client locations.

Key Responsibilities

• Take ownership of issues that require more time or technical depth than our frontline Support Team can provide.
• Troubleshoot and resolve problems involving Windows desktops and servers.
• Troubleshoot and resolve problems involving Active Directory and Group Policy.
• Troubleshoot and resolve problems involving Microsoft 365 and Exchange.
• Troubleshoot and resolve problems involving Microsoft Entra ID and Azure environments.
• Troubleshoot and resolve problems involving firewalls, switches, VLANs, and VPNs.
• Troubleshoot and resolve problems involving DNS and network connectivity.
• Troubleshoot and resolve problems involving backup and recovery systems.
• Troubleshoot and resolve problems involving business applications and third-party software.
• Troubleshoot and resolve problems involving hardware and infrastructure issues.
• Own escalated tickets and help engineers work through complex issues.
• Share knowledge and mentor other team members.
• Help identify recurring problems and opportunities for improvement.
• Work directly with clients and keep them informed throughout an issue.
• Assist with frontline support when escalation volume allows.
• Perform on-site client work when needed.
• Work alongside the Project Team on projects including server deployments and migrations.
• Work alongside the Project Team on projects including network and firewall upgrades.
• Work alongside the Project Team on projects including Microsoft 365 and cloud migrations.
• Work alongside the Project Team on projects including infrastructure replacements.
• Work alongside the Project Team on projects including backup and disaster recovery improvements.
• Work alongside the Project Team on projects including client technology standardization.
• Participate in an on-call rotation, including occasional weekends.
• Occasionally travel to client locations.

Required Experience and Skills

• 4+ years of professional IT support experience.
• Strong troubleshooting skills for Windows workstations and Windows Server.
• Working knowledge of Active Directory.
• Microsoft 365 administration experience.
• Networking knowledge including TCP/IP, DNS, DHCP, VLANs, and VPNs.
• Experience troubleshooting firewalls and network connectivity.
• Ability to independently investigate and resolve unfamiliar technical problems.
• Strong written and verbal communication skills, including professional client communication.
• Strong documentation habits.
• Ability to commute to the West Barnstable, MA office.

Technologies and Tools

• Windows
• Active Directory
• Group Policy
• Microsoft 365
• Exchange
• Microsoft Entra ID
• Azure
• Firewalls
• DNS
• TCP/IP
• DHCP
• VLANs
• VPNs
• Backup and recovery systems
• macOS
• AI technologies and tools
• CompTIA A+, CompTIA Network+, CompTIA Security+, CompTIA Server+, CompTIA Cloud+
• Cisco / CCNA
• Microsoft Certified: Azure Fundamentals

Preferred Qualifications (Nice to Have)

• CompTIA A+, Network+, Security+, Server+, or Cloud+
• Microsoft 365
• Microsoft Azure / Entra ID
• Cisco / CCNA
• Firewall platforms
• Backup and disaster recovery
• macOS support and integration
• AI technologies and tools

Compensation and Benefits

Salary: $80,000–$100,000 per year, based on experience and technical background.

• Health insurance
• 401(k) with company match
• Life insurance
• Long-term disability insurance
• Paid time off
• Incentive compensation through the Works Perks program
• Paid additional compensation for participation in the on-call rotation
• Opportunities to grow into additional Project Team responsibilities
• 401(k)
• 401(k) matching
• Dental insurance
• Tuition reimbursement
• Vision insurance

Schedule, Location, and Shift Availability

• Full-time
• Monday through Friday
• 8-hour shift
• On-site in West Barnstable, Massachusetts (not remote)
• On-call work is compensated in addition to salary, including occasional weekends
• Occasional travel to client locations
• Day Shift (Required)
• Night Shift (Required)
• Overnight Shift (Preferred)

Application Questions

• Have you worked for a managed services provider before?
• Do you understand that this is an in-office position?
• Do you live within 50 miles of West Barnstable, MA?

Experience, Certification, and Commute Requirements

• MSP experience: 4 years (Preferred)
• CompTIA A+: (Preferred)
• CompTIA Network+: (Preferred)
• Microsoft Certified: Azure Fundamentals: (Preferred)
• Ability to commute: West Barnstable, MA (Required)
• Education: High school or equivalent
• Minimum experience: 4 years