Tier 2 IT Support Technician / Server Administrator

Position Overview

The Tier 2 IT Support Technician / Server Administrator is a key technical role within our service organization. This position is responsible for providing advanced desktop, server, and infrastructure support across multiple client environments, while serving as an escalation point for complex technical issues beyond Tier 1.

This role is ideal for a hands-on IT professional with strong experience in Windows Server administration, Microsoft 365, troubleshooting, and client support in an MSP or multi-site environment. The successful candidate will be expected to take ownership of escalated issues, maintain service quality, support clients directly by phone and remotely, and contribute to the stability and improvement of client infrastructure.

Key Responsibilities

• Provide Tier 2 technical support for end-user, workstation, server, and network-related issues across multiple client environments
• Act as an escalation point for Tier 1 support staff, taking ownership of more complex or business-critical incidents
• Answer incoming client support calls in a professional and timely manner, gather accurate information, and either resolve issues directly or route/escalate appropriately
• Deliver remote and occasional onsite support while maintaining a high standard of client communication and service
• Troubleshoot and resolve escalated issues related to:
• Windows workstations
• Windows Server environments
• Microsoft 365
• Active Directory / Group Policy
• File shares, permissions, and user access
• Printers, peripherals, and line-of-business applications
• Remote connectivity / VPN access
• Administer and maintain Windows Server infrastructure, including:
• Active Directory
• DNS / DHCP
• Group Policy
• File and print services
• User and group management
• Basic virtualization support (Hyper-V / VMware)
• Perform server maintenance, patching, monitoring, and health checks
• Support Microsoft 365 administration, including:
• User provisioning / deprovisioning
• Exchange Online administration
• Basic Entra ID / Azure AD administration
• MFA and security policy support
• Escalate or coordinate advanced issues with senior engineers, vendors, or third-party providers when required
• Participate in troubleshooting, remediation, and documentation of infrastructure incidents
• Assist with deployments, upgrades, migrations, and infrastructure improvement projects
• Maintain accurate documentation, ticket notes, and client environment records
• Follow service standards and ensure timely communication with both internal teams and clients
• Contribute to ongoing process improvement and operational maturity within the service desk

Server Administration & Escalation Responsibilities

This role includes direct responsibility for:

• Administration and support of Windows Server environments
• Handling and resolving Tier 2 escalations
• Diagnosing recurring infrastructure issues and recommending long-term fixes
• Supporting backup verification, server recovery coordination, and disaster recovery readiness

Working with internal leadership to ensure escalated issues are addressed with urgency and accountability

On-Call & Client Support Expectations

• Participate in a scheduled on-call rotation to support urgent client issues outside of regular business hours
• Respond to after-hours alerts, incidents, and service-impacting issues in accordance with company standards
• Maintain professionalism and sound judgment when handling urgent support matters by phone or remote access
• Coordinate escalation of critical incidents when additional technical or leadership involvement is required

Qualifications & Experience

Required

• Proven experience in a Tier 2 IT Support, Systems Administrator, or similar infrastructure support role
• Strong hands-on experience with:
• Windows Server administration
• Active Directory
• DNS / DHCP
• Group Policy
• Microsoft 365 administration
• Exchange Online
• Microsoft Entra ID (Azure AD)
• Experience supporting:
• End users in a professional business environment
• Server and workstation troubleshooting
• Escalated incidents and service desk workflows
• Phone-based support and client communication
• Experience with remote monitoring and management tools (RMM)
• Strong understanding of IT infrastructure, troubleshooting methodology, and escalation handling
• Willingness and ability to participate in an on-call support rotation
• Professional experience in an MSP environment or supporting multiple client environments is strongly preferred
• Strong written and verbal communication skills
• Ability to work independently, prioritize effectively, and maintain accountability under pressure

Mandatory Certifications

Candidates must hold a Microsoft server/infrastructure certification:

Mandatory: Microsoft server/infrastructure certification (legacy MCSA/MCSE or equivalent modern Microsoft certification

Or a current equivalent Microsoft certification demonstrating strong competency in:

• Windows Server
• Active Directory
• Group Policy
• Core infrastructure administration

Please note: Microsoft server administration certification is considered a core requirement for this position.

Preferred / Assets

• Experience with VMware and/or Hyper-V
• Experience with backup and disaster recovery platforms
• Knowledge of N-able Backup is considered a strong asset
• Familiarity with Microsoft 365 security and compliance tools
• Experience with firewall, switching, and basic network troubleshooting

Additional certifications in Microsoft 365, Azure, or virtualization are considered a strong asset

What We’re Looking For

• Strong troubleshooting and analytical skills
• A calm, methodical approach to escalated issues
• Ability to take ownership and follow issues through to resolution
• Strong customer service mindset with professional communication
• Confidence handling live client calls and urgent support situations
• Team-oriented, dependable, and accountable
• Someone who can balance day-to-day support with infrastructure awareness and long-term thinking

Why Join Club Support Inc.?

At Club Support Inc., you will be part of a team that values technical excellence, professionalism, responsiveness, and long-term client trust. This role offers the opportunity to work across a variety of client environments while growing your expertise in infrastructure support, server administration, and escalation management.

Job Type: Full-time

Pay: From $65,000.00 per year

Benefits

• Casual dress
• Company events
• Dental care
• Extended health care
• On-site parking
• Paid time off
• Vision care
• Wellness program
• Work from home

Work Location: Hybrid remote in Concord, ON L4K 4C3