Help Desk Support Specialist

💡 Love solving complex IT issues and keeping systems running smoothly? 

We’re hiring a Help Desk Support Specialist for a with a leading Managed Service Provider (MSP) supporting organizations across the GTA. 

You’ll be the go-to expert tackling network, cloud, and infrastructure challenges across diverse client environments, keeping systems stable, secure, and running flawlessly. 

💻 Who You Are 

You’re an experienced IT professional who enjoys switching between clients and technologies. You stay calm under pressure, explain solutions clearly, and take pride in resolving issues fast and keeping clients happy. You’re proactive, resourceful, and always looking for ways to improve systems - not just fix them.  

📍 Work Type 

• Location: Toronto, ON (Fully Onsite - 5 days a week in office)
• Monday to Friday, 9 AM – 5 PM, with after-hours and on-call support on rotation
• Vacancy Type: This role reflects an existing vacancy  

Requirements

🎯 What You’ll Do (Your Superpowers) 

• 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 

⭐ What We’re Looking For (Our Wishlist) 

• 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 
• Certifications such as CompTIA Security+, Network+, Azure Fundamentals, or CCNA are an asset 
• A proactive mindset - someone who doesn’t just fix issues but looks for ways to improve systems and client experiences 

🔥 What Makes This Role Exciting 

• Learning & Growth – Gain hands-on experience across diverse environments, technologies, and client setups 
• Autonomy & Impact – Take ownership of complex tickets and client relationships, making a direct impact every day 

Benefits

• Base Salary: $50,000 - $55,000
• Competitive Vacation and Personal Days
• Health Spending Account to support your well being!

📩 Ready to Elevate Your IT Career? Apply Now! 

At STACK IT Recruitment, we connect top technical talent with standout opportunities across Canada. If you meet at least 70% of the qualifications, we encourage you to apply - we’d love to chat! 

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

AI Use Disclosure:  
STACK IT uses AI-enhanced tools to support initial candidate screening and interview note analysis. All assessments and hiring decisions remain human-led.