Helpdesk Tier 2

This is a remote position.

Position Summary

The Tier 2 IT Technician is a mid-level technical support role responsible for resolving escalated issues from Tier 1, performing advanced troubleshooting, supporting infrastructure systems, and delivering high-quality customer service. This position plays a critical role in keeping client environments operational by balancing reactive support with proactive system improvements.

This role is ideal for someone with strong ConnectWise PSA experience, a working knowledge of MSP environments, and a desire to grow technically while mentoring junior technicians and engaging directly with clients.

Key Responsibilities

Technical Support and Troubleshooting

• Respond to escalated tickets involving workstations, servers, network devices, cloud systems, and line-of-business applications.
  

• Diagnose and resolve complex issues related to:
  

  • Active Directory, Group Policy, permissions, and file shares
    

  • Microsoft 365 (Outlook, Teams, OneDrive, SharePoint)
    

  • Network connectivity (DNS, DHCP, VPN, VLANs)
    

  • Firewall rules, routing, and access control (SonicWall, Meraki, etc.)
    

  • Remote access tools and VPN troubleshooting
    

• Support backup and disaster recovery platforms (Datto, Veeam, Acronis).
  

• Perform server patching, system updates, and performance optimizations.
  

• Escalate complex or unresolved issues to Tier 3 with detailed documentation.
  

Client Interaction and Service

• Act as a direct point of contact for clients needing escalated support.
  

• Deliver clear, timely communication throughout the support lifecycle.
  

• Educate clients on IT best practices, basic troubleshooting, and security hygiene.
  

• Maintain strong relationships by proactively identifying issues and proposing solutions.
  

• Participate in follow-ups to ensure satisfaction and closure of recurring issues.
  

Operational Duties

• Configure and support firewalls, switches, routers, and access points.
  

• Perform workstation and server deployments, including imaging and onboarding.
  

• Maintain compliance with asset tracking, licensing, and software inventory.
  

• Document technical procedures, solutions, and client environments in ITGlue.
  

• Assist in conducting security audits and preventive maintenance.
  

Team Collaboration and Mentorship

• Assist and mentor Tier 1 Technicians, guiding them through troubleshooting steps and escalation criteria.
  

• Participate in team meetings, documentation initiatives, and process improvement efforts.
  

• Contribute to knowledge base articles and SOP development.
  

Ticketing and Process Discipline

• Maintain detailed time entries, work notes, and closure summaries in ConnectWise Manage.
  

• Prioritize workload based on SLA commitments and urgency.
  

• Participate in root cause analysis to reduce repeat issues.
  

• Follow structured escalation procedures per MSP best practices.
  

Requirements

Education and Experience

• Associate degree in IT or equivalent work experience.
  

• 3+ years of IT support experience, ideally within an MSP or service provider.
  

• Strong familiarity with ConnectWise Manage (or equivalent PSA/RMM systems).
  

Technical Proficiency

• Microsoft Windows 10/11, Server 2016/2019/2022
  

• Active Directory, GPOs, DNS, DHCP
  

• Microsoft 365 and Azure AD administration
  

• Network troubleshooting (TCP/IP, VLANs, VPN, firewall configuration)
  

• Remote support tools (RDP, TeamViewer, ConnectWise Control)
  

• Backup systems (Datto, Veeam, Acronis)
  

• Documentation platforms (ITGlue preferred)
  

Certifications (Preferred but Not Required)

• CompTIA A+, Network+, or Security+
  

• Microsoft Azure Fundamentals
  

• ITIL Foundation
  

Soft Skills and Attributes

• Excellent analytical and troubleshooting skills
  

• Strong written and verbal communication
  

• Self-motivated and highly organized
  

• Comfortable handling multiple issues in a fast-paced environment
  

• Strong documentation and process mindset
  

• Able to work independently and collaborate across distributed teams
  

Bonus Qualifications

• Experience in a fast-paced MSP environment
  

• Exposure to virtualization platforms (Hyper-V, VMware)
  

• Familiarity with scripting (PowerShell) or automation tools