Service Desk Technician

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

Job Summary

The Help Desk Technician at Headway Strategy delivers advanced, remote technical support to multiple client environments. This role serves as the initial and primary triage point for users, requiring strong technical troubleshooting skills, excellent customer service, and the ability to work efficiently across diverse systems and industries. The ideal candidate thrives in a fast-paced, client-facing environment and takes ownership of issues through resolution.

Key Responsibilities

• Diagnose and resolve complex desktop, server, and network issues
• Install, configure, and maintain workstations, laptops, printers, and peripheral devices
• Support Microsoft Windows, macOS, and common business applications
• Perform basic administration and troubleshoot Microsoft 365, Active Directory, Azure AD, and email systems
• Perform user account onboarding/offboarding, permissions management, and access control
• Troubleshoot networking issues including DNS, DHCP, TCP/IP, VPNs, and wireless networks
• Use RMM and cybersecurity tools to monitor systems and remediate issues
• Document troubleshooting steps, resolutions, and client environments within the ticketing system and knowledgebase articles
• Collaborate with other support personnel and vendors for complex or unresolved issues
• Deliver professional, customer-focused service while working directly with client stakeholders
• Adhere to MSP processes, SLAs, security policies, and change management procedures

Required Qualifications

• 3+ years of experience in a Help Desk or Technical Support role, preferably within an MSP
• Strong working knowledge of Windows and macOS operating systems
• Experience supporting Microsoft 365, Active Directory, and endpoint management tools
• Solid understanding of networking fundamentals and troubleshooting
• Experience with ticketing systems and managed services workflows
• Extremely high quality of work delivery including attention to detail and documentation
• Excellent verbal and written communication skills
• Excellent team collaboration skills to work together to solve challenges
• Required to submit to a full background check and drug screen resulting in no prior felonies and a completely clean drug screen. Misdemeanors will be assessed in detail on a case-by-case basis.
• Only United States Citizens will be considered for employment due to compliance requirements

Preferred Qualifications

• Prior experience working in an MSP environment
• CompTIA A+, Network+, Security+, or Microsoft certifications
• Experience with Ninja RMM, ConnectWise Manage, and CrowdStrike Falcon
• Familiarity with virtualization (VMware, Hyper‑V) and basic server administration
• PowerShell or scripting experience

Skills & Competencies

• Strong troubleshooting and analytical abilities
• Ability to manage multiple clients and priorities simultaneously
• Customer-first mindset with strong interpersonal skills
• High level of organization and documentation discipline
• Ability to work independently in client environments
• Adaptability in fast‑changing technical environments

Work Environment

• Selected candidate will be required on-site in our Ohio office during standard business hours (Monday through Friday, 8am through 5pm Eastern Time) with a specified lunch hour.
• Only United States Citizens will be considered for employment due to compliance requirements
• Candidates that use tobacco or recreational drugs in any way will not be considered for employment.