Are you someone who enjoys solving technical problems, supporting end users, and keeping IT systems running smoothly behind the scenes?We’re hiring a Desktop Support Specialist to join a growing organization where you’ll play a key role in supporting day‑to‑day IT operations, troubleshooting technical issues, and maintaining critical infrastructure systems.This is an ideal opportunity for someone who enjoys a mix of hands‑on user support, systems administration, and infrastructure maintenance, while working in a fast‑paced, collaborative environment.Who You AreA customer‑focused IT professional who enjoys helping users solve technical issues quickly and effectivelySomeone who thrives in fast‑paced environments and can confidently juggle multiple prioritiesA strong communicator who can explain technical concepts clearly to non‑technical usersDetail‑oriented, organized, and proactive in identifying and resolving issuesA team player who enjoys collaborating while also working independently when neededPassionate about technology and committed to continuous learning and improvementWork TypeLocation: North York, ON (Fully Onsite – 5 days a week in office)Vacancy Type: This role reflects an existing vacancyWhat You’ll DoProvide first‑line technical support for hardware, software, and end‑user related issuesTroubleshoot and resolve desktop, PC, network, and system‑related problemsManage and maintain user accounts, permissions, and group access within Active Directory and related systemsSupport and maintain Microsoft‑based environments including Windows workstations and serversMonitor and maintain infrastructure services including DNS, DHCP, antivirus, backups, and Windows updatesAssist with software implementations, upgrades, and system deploymentsDocument technical issues, resolutions,



and support activities within ticketing and problem management systemsMaintain inventory records for hardware, software, and licensing assetsSupport Office 365 and Azure Active Directory administrationAssist with server, virtualization, and backup infrastructure where requiredEscalate complex technical issues when necessary and support after‑hours maintenance activities as neededWhat We’re Looking For3+ years of experience in desktop support, systems administration, or IT support environmentsStrong knowledge of Microsoft environments including Windows 10/11, Active Directory, and Windows ServerExperience supporting LAN/WAN networks, TCP/IP, DNS, and DHCPExperience with Office 365 and Azure Active Directory administrationStrong troubleshooting, analytical, and problem‑solving skillsExcellent customer service and communication skillsAbility to multitask and prioritize in a fast‑paced support environmentProfessional, patient, and user‑focused approach to technical supportWhat Makes This Role ExcitingVariety: A mix of desktop support, systems administration, and infrastructure workImpact: Play a key role in ensuring business operations and users stay productiveGrowth: Opportunity to expand your infrastructure and systems administration experienceCollaboration: Work closely with internal teams and end users across the organizationBase Salary:$60,000 - $70,000Paid Time Off:Competitive vacation and personal days to maintain a healthy work‑life balanceBenefits Package:Medical, dental, and vision advantages to support your overall well‑beingWe’re proud to support diversity and inclusion.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.#J-18808-Ljbffr

📌 Desktop Support Specialist - C$60,000 - C$70,000 A Year (Winnipeg)
🏢 Stack IT
📍 Winnipeg