Service Desk Technician

Headway Strategy LLC; Fairlawn (OH); On-site; USD 42,000 - 64,000; Full time

Job summary

Headway Strategy LLC is seeking a Help Desk Technician to deliver advanced, remote technical support across multiple client environments. The role acts as the primary triage point with strong troubleshooting and client-facing service, handling issues through resolution in a fast-paced MSP setting.

The ideal candidate has 3+ years in a help desk or technical support role, solid Windows/macOS experience, and familiarity with Microsoft 365, AD, and network fundamentals.

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.
• Excellent communication skills and attention to documentation.

Responsibilities

• Diagnose and resolve desktop, server, and network issues.
• Install, configure, and maintain workstations, laptops, printers, and peripherals.
• Support Windows, macOS, and common business applications.
• Troubleshoot Microsoft 365, Active Directory, Azure AD, and email systems.
• Onboard/offboard users and manage permissions and access control.
• Troubleshoot DNS, DHCP, TCP/IP, VPNs, and wireless networks.
• Utilize RMM and cybersecurity tools to monitor and remediate issues.
• 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.

Skills

Troubleshooting

Customer service

Documentation

Team collaboration

Communication

Multitasking

Independent work

Tools

Ninja RMM

ConnectWise Manage

CrowdStrike Falcon

VMware

Hyper-V

PowerShell

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.