OverviewLove solving complex IT issues and keeping systems running smoothly? We’re hiring a Help Desk Support Specialist for 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 secure, secure, and running flawlessly.Who You AreYou’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 TypeLocation: 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 rotationVacancy Type: This role reflects an existing vacancyWhat You’ll DoProvide Tier 2 technical support across multiple client environments in an MSP settingTroubleshoot, diagnose, and resolve complex issues involving hardware, software, and networksManage 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 managementCollaborate with clients and vendors for escalations and project implementationsParticipate in client onboarding, migrations, and system upgradesDocument fixes, update ticketing systems,



and contribute to the internal knowledge baseExperience with virtualization platforms such as VMware and Hyper‑VUtilize automation and scripting (PowerShell, Bash) to streamline repetitive tasks and optimize performanceWhat We’re Looking For2+ years of experience providing IT support across multiple client environments – ideally within an MSP or IT services organizationStrong technical foundation in Microsoft 365, Active Directory, networking, and endpoint managementHands‑on experience troubleshooting hardware, software, and network issues across Windows, macOS, and mobile environmentsFamiliarity with VPNs, VLANs, firewalls (SonicWall, Sophos, Unifi), and general cybersecurity best practicesExposure to virtualization (VMware, Hyper‑V) and automation or scripting tools (PowerShell, Bash)Experience managing client escalations, migrations, and system upgrades with professionalism and clear communicationProficiency with Remote Monitoring & Management (RMM) tools such as N-Central, ConnectWise, or SolarWindsCertifications such as CompTIA Security+, Network+, Azure Fundamentals, or CCNA are an assetA proactive mindset – someone who doesn’t just fix issues but looks for ways to improve systems and client experiencesWhy This Role ExcitesLearning & Growth– Gain hands‑on experience across diverse environments, technologies, and client setupsAutonomy & Impact– Take ownership of complex tickets and client relationships, making a direct impact every dayBenefitsBase Salary : $50,000 – $55,000Competitive Vacation and Personal DaysHealth Spending Account to support your well-beingDiversity & InclusionWe’re proud to support diversity and inclusion. Need accommodation during the hiring process? Just let us know – we’re here to help.#J-18808-Ljbffr

📌 Help Desk Support Specialist - C$50,000 - C$55,000 A Year (Winnipeg)
🏢 STACK IT Recruitment
📍 Winnipeg