Senior IT Manager

We are looking for an IT Manager or Senior IT Manager to lead Caseware’s global IT function from our Toronto headquarters. This is a hands on leadership role, not a purely managerial one. You will own the strategy, roadmap, and operational performance of IT globally, while also bringing the technical credibility to get involved in architecture decisions, escalated incidents, and infrastructure challenges when needed. 

You will lead a team across service desk, ITSM, infrastructure, and operations. Your two direct reports, the ITSM and Service Desk Lead and the Infrastructure and Operations Lead, each own a major functional area. Your role will be to set direction, remove blockers, develop the team, and ensure the full IT function operates effectively. 

Our environment is modern and hybrid. We are cloud first where it makes sense, on premise where it matters, and continuously modernizing. Our stack includes AWS, Azure, VMware, Hyper V, Cisco UCS, HCI platforms, and enterprise systems that support our global employee base. 

❗This is a Full time position 

❗ This is an Existing Vacancy 

This is a hybrid role requiring the successful candidate to work 3 days a week in our Toronto office, located at 351 King Street East, Suite 1100, Toronto, ON. M5A 2W4

 Lead Caseware’s global IT function across service desk, ITSM, infrastructure, cloud, and operations 

• Own the IT roadmap, including modernization, service delivery, operational resilience, and global scalability 

• Manage and develop IT leads and technical teams across multiple functional areas 

• Provide technical leadership across AWS, Azure, VMware, Hyper V, Cisco UCS, HCI, networking, and enterprise systems 

• Oversee escalated incidents, root cause analysis, problem management, and major service disruptions 

• Improve service desk performance, ticket resolution, ITSM processes, asset management, and employee support 

• Partner with Security, Engineering, Product, Finance, People, and business leaders to ensure IT supports company growth 

• Drive automation, process improvements, vendor management, cost optimization, and platform consolidation 

• Ensure IT operations align with security, privacy, compliance, and audit requirements 

• Introduce practical AI and automation into IT operations to improve efficiency, support quality, and employee experience 

AI and Automation Focus 

• Identify opportunities to use AI across service desk, ticket routing, knowledge management, infrastructure operations, and reporting 

• Evaluate AI enabled tools that improve response times, reduce manual work, and help IT scale globally 

• Partner with Security and Compliance to ensure responsible AI use, data protection, and proper governance 

• Separate useful AI capabilities from hype, with a focus on measurable business value 

• Strong hands on technical background across hybrid enterprise IT environments 

• Experience with AWS, Azure, VMware, Hyper V, Cisco UCS, HCI, networking, and enterprise systems 

• Strong understanding of ITSM, incident management, change management, problem management, and service delivery 

• Experience managing technical leads, engineers, infrastructure teams, or service desk teams 

• Ability to operate at both strategic and hands on levels 

• Experience modernizing infrastructure, improving IT operations, and scaling technology services 

• Strong communication, vendor management, stakeholder management, and decision making skills 

• Experience with automation, AI enabled tools, or workflow improvements within IT operations