Service Desk Technician

Job Description

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.

NOTE: Applications will be accepted through 09/30/2026, at which time initial interview will be scheduled.

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.