Headway Strategy · 2 weeks ago
Help Desk Technician – Tier 2 (In-Office)
Fairlawn, Ohio, United States
Full-time
Onsite
Mid Level
$55K/yr - $55K/yr
3+ years expHeadway Strategy is seeking a Help Desk Technician (Tier 2) to deliver advanced technical support to multiple client environments. This role requires strong troubleshooting skills and excellent customer service, acting as an escalation point for Tier 1 support while collaborating with Tier 3 engineers for complex issues.
Management Consulting
No H1B
U.S. Citizen Only
Responsibilities
Act as the primary escalation point for Tier 1 technicians across multiple client environments
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
Administer and troubleshoot Microsoft 365, Active Directory, Azure AD, and email systems
Perform user account provisioning, permissions management, and access control
Troubleshoot networking issues including DNS, DHCP, TCP/IP, VPNs, and wireless networks
Use MSP tools and RMM platforms to monitor systems and remediate issues
Document troubleshooting steps, resolutions, and client environments within the ticketing system
Collaborate with Tier 3 engineers 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
Qualification
Required
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
Preferred
Prior experience working in an MSP environment
CompTIA A+, Network+, Security+, or Microsoft certifications
Experience with Ninja RMM, Connectwise Manage, and Synology backup solutions
Familiarity with virtualization (VMware, Hyper-V) and basic server administration
PowerShell or scripting experience
Company
Headway Strategy
Headway Strategy is a boutique management consulting firm dedicated to supporting businesses through proper strategy and operational evolutions needed to generate a competitive market approach and future viability.
11-50 employees
Funding
Current Stage
Early StageCompany data provided by crunchbase