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Randstad Logo Randstad · IT - Administration

Senior Program Manager - Transformation

Canada, Mississauga 58.21 - 74.38 USD / Hour · Job Posted July 08, 2026
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Job Description

Our client is seeking a highly tenured, visionary Senior Program Manager - Transformation to lead a series of high-profile, novel business value streams cutting across Supply Chain, Merchandising, Store Operations, and Workforce Optimization. This is not a traditional IT implementation role. This initiative is heavily business-led and reports directly to an Executive Steering Committee comprised of the entire C-suite and Executive Leadership Team (ELT). We are looking for an ambiguous-thriving leader who can build a path where one does not yet exist, driving macro-level Organizational Change Management (OCM) to achieve true business reinvention. Duration: 12-Month Contract (Multi-year initiative) Work Arrangement: Hybrid (2-3 days per week on-site at the Mississauga, ON office).

Job Responsibility

  • Executive Facilitation: Partner directly with the VP of Technology Transformation and the C-suite Executive Steering Committee to translate high-level strategic vision into a concrete execution roadmap
  • Cross-Functional Program Delivery: Oversee a portfolio of complex, multi-million-dollar value streams including advanced supply chain visibility platforms, automated merchandising, store operations, and next-generation labor/workforce optimization
  • Macro Change Leadership (OCM): Act as the primary champion for driving organizational change across the enterprise. Leverage structured frameworks, empathy, and influence to successfully pivot corporate culture and frontline retail operations
  • Navigating Ambiguity: Establish structure, governance, and delivery frameworks for fast-moving, "novel" or experimental corporate initiatives where no market blueprint yet exists
  • Resource & Vendor Governance: Collaborate with internal PMO leaders and external strategic consulting partners to effectively manage complex resourcing pools, multi-million-dollar financial tracking, and tier-1 vendor deliverables.

Requirements

  • 10+ years of progressive program management leadership, with a proven track record of steering massive, multi-year strategic innovation or business transformation programs
  • Direct experience managing mega-programs with budgets scaling from $10M to $100M+
  • Extensive, deep-dive experience navigating the complexities of a large-scale enterprise retail or grocery ecosystem (Supply Chain, Merchandising, or Field Operations)
  • Expert-Level Change Management (OCM): Exceptional soft skills with a proven, referenceable capability to drive enterprise-wide organizational change, overcome internal resistance, and implement complex new operating models
  • Executive Presence: High credibility and polish in guiding, presenting to, and influencing C-suite and Executive-level steering committees
  • Core Focus: Please note that deep technical expertise in Generative AI or Agentic workflows is not a prerequisite. Success hinges on a track record of corporate reinvention and high-level change.

Nice to have

  • Active Change Management validation or a PMP certification
  • Familiarity with enterprise data platforms or advanced supply chain visibility architectures (such as Palantir Foundry)
  • Experience leading pilot programs for cutting-edge, experimental, or net-new software in a corporate environment
  • Bilingualism (English / French) is considered a strong asset.

What we offer

  • C-Suite & ELT Visibility: Partner directly with Executive Vice Presidents and the C-suite, commanding high-stakes strategic conversations and visibility
  • Bleeding-Edge Innovation Portfolio: Champion enterprise-wide GenAI and advanced technology pilots that will redefine the future of the retail industry
  • True Business Reinvention: Lead a program focused on organizational transformation and corporate strategy rather than strict technical configuration
  • Long-Term Strategic Impact: Drive a multi-million-dollar portfolio from its earliest, most ambiguous phases through to real-world corporate adoption.
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