Help Desk Administrator
Winsor Consulting Group, LLC
Help Desk Administrator
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:
- Windows and macOS operating systems
- Microsoft 365 (Exchange, OneDrive, SharePoint, Teams, Intune)
- Networking fundamentals (LAN/WAN, DNS, DHCP, VPN, Wi-Fi)
- Active Directory and Group Policy
- Virtualization 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 on-call rotation to provide after-hours 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 on-site engagements
Experience:
- 2 to 4 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
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