Help Desk Administrator

Department: Service Operations

Reports to: Service Operations Manager

Job Description

The Help Desk Administrator is a Tier 2 technician responsible for handling escalated service requests, troubleshooting complex technical issues, and providing support and mentorship to Tier 1 staff. This position plays a key role in maintaining service quality and client satisfaction by ensuring technical issues are resolved efficiently and accurately. In addition to day-to-day support duties, this role may assist with internal and client-facing projects and must maintain clear, professional communication with both clients and internal teams.

Job Duties:

• Provide advanced troubleshooting and resolution for escalated issues from Tier 1 technicians
• Support and resolve issues related to: o Windows and macOS operating systems
• Microsoft 365 (Exchange, OneDrive, SharePoint, Teams, Intune) oNetworking fundamentals (LAN/WAN, DNS, DHCP, VPN, Wi-Fi)
• Active Directory and Group Policy oVirtualization platforms (basic support for Hyper-V, VMware)
• PC/laptop hardware and peripheral devices
• Image, configure, and deploy workstations and laptops
• Deliver clear and timely updates within the ticketing system (e.g., ConnectWise Manage)
• Maintain high levels of customer service and professionalism in all client communications
• Participate in internal training and documentation efforts
• Provide guidance, mentoring, and support to Tier 1 Help Desk staff
• Identify recurring issues and recommend process or technical improvements
• Perform remote support using remote desktop and RMM tools
• Participate in the department’s oncall rotation to provide afterhours support as needed
  
  

Preferred Skills:

• Strong working knowledge of Windows desktop OS and Microsoft 365
• Familiarity with Exchange Online, Active Directory, and basic server administration
• Understanding of core networking concepts (TCP/IP, DNS, DHCP, VPN)
• Experience with RMM and PSA tools (e.g., ConnectWise Automate/Manage)
• Excellent troubleshooting and logical thinking skills
• Ability to clearly document work and resolutions
• Professional verbal and written communication skills
• Ability to work independently and collaboratively within a team
• Strong customer service orientation and attention to detail
• Ability to represent Winsor Consulting in a professional manner, especially during onsite engagements
  
  

Experience:

• 24 years of experience in a technical support role, preferably within a Managed Services Provider (MSP)
• Experience handling Tier 2 or escalated support requests
• Experience with remote desktop and remote support tools (e.g., ScreenConnect, TeamViewer)
• Familiarity with scripting or automation tools is a plus
  
  

Education:

• Associate's Degree in Information Technology or equivalent experience. Bachelor's Degree in IT preferred.
• Preferred Certifications CompTIA A+, Network+, Server+, Microsoft 365 Certified: Modern Desktop Administrator Associate