Senior IT Manager

Caseware • Toronto, ON

15h • Hybrid

About The Position

Caseware is seeking an IT Manager or Senior IT Manager to lead its global IT function from its Toronto headquarters. This is a hands-on leadership role where you will be responsible for the strategy, roadmap, and operational performance of IT globally. You will also be involved in architecture decisions, escalated incidents, and infrastructure challenges. You will lead a team across service desk, ITSM, infrastructure, and operations, setting direction, removing blockers, developing the team, and ensuring the IT function operates effectively. The environment is modern and hybrid, with a cloud-first approach where appropriate, and continuous modernization efforts. The technology stack includes AWS, Azure, VMware, Hyper V, Cisco UCS, HCI platforms, and enterprise systems.

Requirements

• Experience leading IT, infrastructure, service desk, ITSM, or technology operations teams in a global or multi site environment
• 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
• Experience in SaaS, fintech, software, audit, accounting, or regulated technology environments
• Experience supporting global offices and distributed teams
• Familiarity with ITIL, SOC 2, ISO, COBIT, or related operational frameworks
• Experience with endpoint management, identity, collaboration tools, and enterprise productivity platforms

Responsibilities

• 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
• 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

Benefits

• medical
• vision
• dental
• life insurance
• disability coverage
• company matching retirement savings
• employee assistance programs

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed