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About the Role

Join a leading Managed Service Provider (MSP) in the GTA as a Help Desk Support Specialist. You will be the primary contact for resolving network, cloud, and infrastructure issues across various client environments, ensuring system stability and security.

Responsibilities

• Provide Tier 2 technical support across multiple client environments in an MSP setting.
• Troubleshoot, diagnose, and resolve complex issues involving hardware, software, and networks.
• Manage and support Microsoft 365, including user management, security, and hybrid deployments (Intune, Defender 365, Azure).
• Support Active Directory, domain configurations, and workstation environments (Windows, macOS, and mobile).
• Configure and maintain network devices (routers, switches, firewalls – SonicWall, Sophos, Unifi).
• Ensure cybersecurity best practices, including SPAM filtering, threat detection, and vulnerability management.
• Collaborate with clients and vendors for escalations and project implementations.
• Participate in client onboarding, migrations, and system upgrades.
• Document fixes, update ticketing systems, and contribute to the internal knowledge base.
• Experience with virtualization platforms such as VMware and Hyper-V.
• Utilize automation and scripting (PowerShell, Bash) to streamline repetitive tasks and optimize performance.

Requirements

• 2+ years of experience providing IT support across multiple client environments, ideally within an MSP or IT services organization.
• Strong technical foundation in Microsoft 365, Active Directory, networking, and endpoint management.
• Hands-on experience troubleshooting hardware, software, and network issues across Windows, macOS, and mobile environments.
• Familiarity with VPNs, VLANs, firewalls (SonicWall, Sophos, Unifi), and general cybersecurity best practices.
• Exposure to virtualization (VMware, Hyper-V) and automation or scripting tools (PowerShell, Bash).
• Experience managing client escalations, migrations, and system upgrades with professionalism and clear communication.
• Proficiency with Remote Monitoring & Management (RMM) tools such as N-Central, ConnectWise, or SolarWinds.
• A proactive mindset - someone who doesn’t just fix issues but looks for ways to improve systems and client experiences.

Skills

• Microsoft 365
• Active Directory
• Networking
• Endpoint Management
• Hardware Troubleshooting
• Software Troubleshooting
• Network Troubleshooting
• Windows
• macOS
• Mobile Environments
• VPNs
• VLANs
• Firewalls
• SonicWall
• Sophos
• Unifi
• Cybersecurity Best Practices
• VMware
• Hyper-V
• PowerShell
• Bash
• Remote Monitoring & Management (RMM) tools
• N-Central
• ConnectWise
• SolarWinds

Location

• Toronto, ON

Work Type

• Fully Onsite
• Full-time

Experience Level

• 2+ years of experience

Education Level

• CompTIA Security+ certification is an asset
• Network+ certification is an asset
• Azure Fundamentals certification is an asset
• CCNA certification is an asset

Salary/Compensations

• $50,000 - $55,000

Benefits

• Competitive Vacation and Personal Days
• Health Spending Account

About the Company

• At STACK IT Recruitment, we connect top technical talent with standout opportunities across Canada.

Equal Opportunity

• We’re proud to support diversity and inclusion. Need accommodation during the hiring process? Just let us know - we’re here to help.