IT Support Specialist

Who we need

Reporting to the Manager, IT Support Services, we are hiring an IT Support Specialist on a two-year contract. In this role, you will ensure systems remain secure, stable, and available, while supporting initiatives such as cloud migration, network upgrades, and automation.

You will provide day-to-day technical support across multiple programs and locations, troubleshooting issues, supporting infrastructure and cloud platforms, and maintaining end-user devices. Your work will directly enable teams to deliver essential community services without interruption.

This existing vacancy is a full-time, hybrid position, with on‑site work on Mondays plus two additional in‑office days and two remote days per week. Initial onboarding and training will take place fully on‑site. The role requires flexibility to adjust on‑site days as needed, travel to nearby locations outside the downtown Toronto core, and provide support outside standard business hours during peak project periods.

Technical challenges. You want to play a key role in critical technology projects. You will be part of a digital transformation that includes LAN/WAN upgrades, cloud migration, Power Shell automation, SharePoint adoption, and expanded documentation and process design.

Growth. You want to broaden and deepen your experience in cloud services, automation, enterprise support, custom applications, scripting, and a wide range of technologies. You will work with a robust IT team and directly support over 200 devices, gaining exposure to systems and projects rarely available in a single role.

Meaningful impact. You want to empower teams with access to reliable, cutting‑edge technology and tools so they can focus on our mission. You will enhance the daily technology experience for staff across community programs, enabling the organization to transform its approach to technology. You will play a central role in ensuring stability, security, accessibility, and operational continuity, directly contributing to improved outcomes for their community‑based clients.

• Deliver end‑to‑end technical support. You will respond to and resolve a wide range of technical issues spanning devices, applications, cloud platforms, and network connectivity. From initial intake through final resolution, you will retain ownership of each request, providing support both remotely and onsite for challenges related to access, email, printing, and device performance. All incidents and service requests will be tracked, updated, and documented through an ITSM platform such as Jira Service Management.
• Operate and improve core systems and infrastructure. You will deploy, configure, and support laptops, iPads, AV equipment, and network hardware, including switches, routers, firewalls, wireless access points, and newly introduced endpoints. Your work will support ongoing LAN and WAN modernization initiatives, covering installation, configuration, troubleshooting, and maintenance, while contributing to the organization’s overall security posture.
• Manage and automate cloud environments. You will administer Microsoft 365, Azure AD, and SharePoint environments throughout and beyond the migration of five legacy servers to SharePoint. Responsibilities include account provisioning, license assignment, policy configuration, and service optimization. You will build automation using Power Shell and contribute to a long‑term cloud strategy, including preparing for a future transition from Azure to AWS.
• Support business‑critical applications. You will troubleshoot and support both proprietary and commercial applications that underpin daily operations. This includes working closely with internal stakeholders and external vendors to resolve issues, implement enhancements, and deploy updates. Full training will be provided on specialized systems and workflows.
• Oversee device and access lifecycle management. You will play a key role in onboarding and off‑boarding by preparing devices, provisioning user accounts, managing permissions, issuing equipment, and ensuring accurate access configuration. You will help maintain…