Overview:
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.
About the opportunity: Director, Information Technology and Digital Transformation
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.
Location: Mississauga
Role Responsibilities:
Technology Strategy & Direction
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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.
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Identify opportunities where technology, automation, analytics, and AI can improve productivity, compliance, and competitive differentiation, and bring forward business cases for prioritization.
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Provide leadership and oversight for technology governance, architecture standards, and enterprise technology decision-making within the role's mandate.
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Ensure technology investments are prioritized based on business value, risk reduction, operational efficiency, and strategic alignment.
Enterprise Architecture & Technology Governance
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Establish and maintain technology standards, reference architectures, and governance processes across the enterprise.
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Ensure technology solutions are scalable, supportable, secure, and aligned with long-term business requirements.
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Oversee Software Development Lifecycle (SDLC) governance, source code management, release management, and deployment controls.
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Drive technology rationalization and reduction of technical debt through platform consolidation and modernization initiatives.
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Maintain oversight of enterprise SaaS platforms and ensure effective integration across business systems.
IT Operations & Service Delivery
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Oversee enterprise IT service delivery across applications, infrastructure, networks, and SaaS platforms.
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Ensure systems are stable, secure, and performant to support retail, field, and corporate environments.
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Establish and maintain governance for incident management, change management, and release processes.
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Drive continuous improvement in service reliability, responsiveness, and user experience
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Ensure technology services support a geographically distributed workforce across retail, field, and corporate environments while maintaining consistent service levels and user experience.
Digital Transformation, Automation & AI Enablement
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Lead enterprise modernization initiatives including cloud adoption, platform consolidation, workflow automation, and digital workplace transformation.
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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 developed solutions.
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Partner with business leaders to identify automation opportunities that improve productivity, reduce manual effort, and enhance data quality.
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Deliver scalable, integrated solutions that support analytics, reporting, and operational decision-making, in partnership with the Business Intelligence and Data Services teams.
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Balance innovation with operational resilience, cybersecurity requirements, compliance obligations, and cost management.
Financial Stewardship & Vendor Management
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Manage the operational technology budget and contribute to the annual technology planning and investment prioritization led by the Executive Leadership Team.
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Establish business cases and ROI measures for major technology investments and transformation programs.
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Identify opportunities to optimize cost through consolidation, automation, and strategic sourcing.
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Manage vendor relationships, contract renewals, and licensing across the technology portfolio.
Cross Functional Partnership & Enablement
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Build strong partnerships with Operations, Client Services, Finance, HR, Sales, and Analytics teams.
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Act as a trusted technology advisor to business leaders, translating needs into scalable, secure solutions.
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Represent IT in cross functional planning forums, transformation initiatives, and program reviews.
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Ensuring technology decisions reflect both business value and operational reality.
Leadership & Team Development
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Lead, coach and develop a technology team, alongside external partners responsible for the delivery of enterprise technology services.
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Foster a culture of accountability, collaboration, continuous improvement, and customer service excellence.
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Establish succession planning, skills development, and workforce planning strategies that support future organizational growth.
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Ensure team objectives, performance measures, and priorities are aligned to corporate goals.
What You Bring to the Table
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10+ years of progressive Information Technology experience, including leadership responsibility for enterprise infrastructure, cybersecurity, applications, or digital transformation initiatives.
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5+ years in a senior leadership role managing cross-functional technology teams, including experience leading through managers or team leads.
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Experience leading enterprise cloud transformation initiatives utilizing Microsoft Azure and Microsoft 365 platforms.
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Experience operating within a regulated or compliance-driven environment, including responding to clients or external security and audit requirements.
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Experience supporting ISO 27001 or comparable security and governance frameworks.
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Experience managing enterprise service management platforms and ITIL-based processes.
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Experience evaluating and governing emerging technologies, including Artificial Intelligence and automation platforms.
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Experience managing technology budgets and contributing to enterprise-level financial planning.
- Experience supporting geographically distributed workforces across retail, field, and corporate environments.
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Bachelor’s degree in information technology, Computer Science, or related field or equivalent experience.
Preferred Certifications
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ITIL Foundation or higher
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CISSP, CISM, CRISC, or equivalent security certification
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Microsoft Azure certification
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ISO 27001 Lead Implementer or Lead Auditor (asset)
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Project Management certification (PMP or equivalent) (asset)
Let's Talk Perks
The salary range for this role is $150K to $170K, your final compensation will reflect your years of experience and beyond the numbers, we’re proud to offer a holistic package that includes:
- Generous time off: Start with 3 weeks of vacation.
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Comprehensive benefits package: Includes medical, dental, vision and a health spending account.
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Retirement support: Company-sponsored RRSP matching program to help build your financial future.
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Award-winning culture: Proud to be one of Canada’s Best Managed Companies for 8 years running — now a Platinum Club member.
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Invested in you: Structured employee development programs designed to help you thrive.
We’re committed to supporting your success every step of the way. What are the next steps?
Interview Steps:
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Step 1: If your profile is a match, we will invite you for a first conversation with the recruiter.
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Step 2: The next step is an in-person interview with the SVP, Data and Technology.
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Step 3: Final step is an in-person interview with the Chief Operating Officer.
If this sounds like you and you’re excited to be a member of our team, please apply now.
We thank all interested applicants; however, only qualified candidates will be contacted. This position requires successful completion of a criminal background check.
Disclaimer: As part of our recruitment process, we utilize artificial intelligence (AI)-based tools to assist with certain stages, including initial resume screening and skills-matching assessments. These tools are designed to help our hiring team identify candidates whose experience and qualifications align closely with the requirements of the role. Please note that all final hiring decisions are made by our recruitment team. The preceding job description has been designed to indicate the general nature and level of work performed by employees within this job. It is not designed to contain or be interpreted as a comprehensive inventory of all duties, responsibilities and qualifications required of employees assigned to this job. In compliance with Ontario’s Bill 190, we confirm that this posting represents a current existing vacancy within our organization.
