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