MSP Help Desk Technician — Windows/macOS Expert

Headway Strategy; Fairlawn (OH); On-site; USD 48,000 - 56,000; Full time

Job summary

Headway Strategy is seeking a Help Desk Technician to provide remote, client-facing technical support for multiple environments. The role acts as the initial triage point, diagnosing issues and guiding users to resolution with strong troubleshooting and documentation.

The ideal candidate will have 3+ years in a help desk or MSP setting, solid Windows/macOS skills, experience with 365/AD, and familiarity with RMM and security tools. Local Ohio on-site presence is required.

Qualifications

• 3+ years in a Help Desk or Technical Support role (MSP preferred).
• Strong knowledge of Windows and macOS.
• Experience with Microsoft 365 and Active Directory.
• Solid networking fundamentals and troubleshooting.

Responsibilities

• Diagnose and resolve desktop, server, and network issues.
• Install, configure, and maintain workstations and peripherals.
• Support Windows, macOS, and business apps.
• Troubleshoot Microsoft 365, Active Directory, and email systems
• Onboard/offboard users, manage permissions and access.
• Troubleshoot DNS, DHCP, TCP/IP, VPNs, and Wi-Fi issues.
• Utilize RMM and cybersecurity tools to monitor and remediate.
• Document steps and resolutions in ticketing system and knowledgebase
• Collaborate with peers and vendors for complex issues
• Provide professional, customer-focused service to client stakeholders
• Adhere to MSP processes, SLAs, and security policies

Skills

Troubleshooting

Customer service

Documentation

Independent work

Education

CompTIA A+

Network+

Security+

Microsoft certifications

Tools

Ninja RMM

ConnectWise Manage

CrowdStrike Falcon

Job description

Headway Strategy is seeking a Help Desk Technician to provide remote, client-facing technical support for multiple environments. The role acts as the initial triage point, diagnosing issues and guiding users to resolution with strong troubleshooting and documentation.

The ideal candidate will have 3+ years in a help desk or MSP setting, solid Windows/macOS skills, experience with 365/AD, and familiarity with RMM and security tools. Local Ohio on-site presence is required.