Job Description
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