Support Technician (In-Office)

The Help Desk Technician at Headway Strategy delivers advanced, remote technical support to multiple client environments. This role serves as an escalation point for more junior analysts, 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., * 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

• 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 MSP workflows
• Excellent verbal and written communication skills
• Required to pass full background check and drug screen, * Prior experience working in an MSP environment
• CompTIA A+, Network+, Security+, or Microsoft certifications
• Experience with Ninja RMM, Connectwise Manage, and SentinelOne
• 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

• Selected candidate will be required on-site in our Fairlawn, Ohio office during standard business hours (Monday through Friday, 8am through 5pm Eastern Time).
• 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.