Director of Information Technology

At OSL Retail Services, we believe people are the heart of everything we do, and it is an exciting time to be part of something special! Our momentum is growing, and is fueled by innovation, collaboration, and a shared entrepreneurial spirit that drives real results. Founded in 2012 in Mississauga, Ontario, OSL delivers customized sales solutions in retail, direct sales, and customer acquisition, all built on a foundation of integrity, respect, and passion.

Our culture thrives on connection, purpose, and growth. If you’re looking for a place where your talents are valued, your ideas matter, and your career can grow, we’d love to meet you.

OSL Retail Services is a technology-enabled sales and retail services organization supporting some of North America’s leading brands. As Director, Information Technology and Digital Transformation, you will lead the delivery and evolution of enterprise technology services that support corporate operations, field teams, client programs, analytics, and business transformation initiatives.

Reporting to the SVP, Data and Technology, you will lead a team of managers and technical leads, alongside external partners and managed service providers. You will be responsible for ensuring OSL’s technology ecosystem, including cloud platforms, cybersecurity, enterprise applications, service management, AI governance, and digital workplace services, remains secure, scalable, resilient, and aligned to business objectives.

This role is the critical bridge between the SVP’s strategic direction and day to day technology delivery, translating strategy into measurable outcomes, while maintaining a strong focus on governance, operational excellence and value realization.

• Contribute to and execute the multi-year technology strategy in partnership with the SVP, Data and Technology, translating strategic direction into delivery roadmaps, programs, and measurable outcomes.
• Identify opportunities where technology, automation, analytics, and AI can improve productivity, compliance, and competitive differentiation, and bring forward business cases for prioritization.
• Provide leadership and oversight for technology governance, architecture standards, and enterprise technology decision-making within the role's mandate.
• Ensure technology investments are prioritized based on business value, risk reduction, operational efficiency, and strategic alignment.

• Establish and maintain technology standards, reference architectures, and governance processes across the enterprise.
• Ensure technology solutions are scalable, supportable, secure, and aligned with long-term business requirements.
• Oversee Software Development Lifecycle (SDLC) governance, source code management, release management, and deployment controls.
• Drive technology rationalization and reduction of technical debt through platform consolidation and modernization initiatives.
• Maintain oversight of enterprise SaaS platforms and ensure effective integration across business systems.

• Oversee enterprise IT service delivery across applications, infrastructure, networks, and SaaS platforms.
• Ensure systems are stable, secure, and performant to support retail, field, and corporate environments.
• Establish and maintain governance for incident management, change management, and release processes.
• Drive continuous improvement in service reliability, responsiveness, and user experience
• Ensure technology services support a geographically distributed workforce across retail, field, and corporate environments while maintaining consistent service levels and user experience.

• Lead enterprise modernization initiatives including cloud adoption, platform consolidation, workflow automation, and digital workplace transformation.
• Operationalize and mature OSL's established enterprise AI governance program, aligned to ISO 42001 and the NIST AI Risk Management Framework, covering employee AI use, AI capabilities within SaaS platforms, and internally…