Senior IT Manager

Caseware is seeking a Senior IT Manager to lead its global IT function from its Toronto headquarters. The successful candidate will own the IT strategy, roadmap, and operational performance of IT globally, and bring technical credibility to get involved in architecture decisions, escalated incidents, and infrastructure challenges.

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

Benefits

• Comprehensive benefits package including medical, vision, dental, life insurance, disability coverage, company matching retirement savings, and employee assistance programs
• Discretionary annual bonus
• Equity participation
• Flexible work options
• Generous time-off policies
• Recognition and rewards
• Remote opportunities