IT & Digital Transformation Director

OSL Retail Services Inc.; Mississauga; On-site; CAD 150,000 - 170,000; Full time

Benefits offered by this job

Salary range $150K-$170K CAD

Professional development

Job summary

OSL Retail Services Inc. is seeking a Director of Information Technology and Digital Transformation in Mississauga.

You will lead enterprise technology services, cloud adoption, cybersecurity, and AI governance, aligning technology with business objectives and regulatory requirements. You will manage a team of managers and external partners, drive platform modernization, and ensure secure, scalable technology across corporate and field operations.

Qualifications

• Progressive IT leadership experience.
• Experience with enterprise cloud transformations.
• Experience in regulated environments and audits.
• ISO 27001 or similar security governance familiarity.
• ITIL-based service management knowledge.

Responsibilities

• Lead multi-year technology strategy and delivery roadmaps.
• Oversee governance, architecture standards, and platform decision-making.
• Manage IT operations across applications, infra, networks, and SaaS.
• Drive modernization, automation, and AI governance in line with standards.
• Manage budgets, vendors, and cross-functional partnerships.

Skills

Leadership

Cloud strategy

IT governance

Cybersecurity

Budget management

Vendor management

ISO 27001 experience

ITIL processes

Education

Bachelor’s degree in IT/CS

Tools

Microsoft Azure

Microsoft 365

Job description

OSL Retail Services Inc. is seeking a Director of Information Technology and Digital Transformation in Mississauga.

You will lead enterprise technology services, cloud adoption, cybersecurity, and AI governance, aligning technology with business objectives and regulatory requirements. You will manage a team of managers and external partners, drive platform modernization, and ensure secure, scalable technology across corporate and field operations.