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Director, Program Management

Hybrid in Canada: Toronto
Program Management
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We are seeking a Director, Program Management to lead the successful delivery of large-scale, multi-phase programs spanning store technology rollouts, AI-driven initiatives, and customer-facing solutions, while driving alignment across technical, operational, and business teams to achieve company goals and objectives.

Req# 1079343844

Responsibilities
  • Strategically lead the successful delivery of large-scale, multi-phase programs, ensuring alignment with company goals and objectives
  • Deliver impactful outcomes through meticulous planning, collaborative execution, and risk mitigation
  • Manage concurrent programs spanning store technology rollouts, AI-driven initiatives, and customer-facing solutions
  • Leverage change management best practices to ensure seamless adoption of new technologies across the organization
  • Bring real-world AI delivery experience, implementing solutions such as machine learning models, predictive analytics engines, and intelligent automation into retail and store operations
  • Work with data science and engineering teams to deploy AI-powered tools that optimize areas such as inventory forecasting, customer engagement, fraud detection, and POS efficiency
  • Collaborate with stakeholders to identify business challenges that can be solved with scalable AI solutions
  • Drive the planning, execution, and successful delivery of store technology solutions, including those involving POS systems, payment platforms, and customer-facing technologies
  • Oversee the implementation of next-generation, cloud-enabled store solutions while ensuring compatibility with existing systems
  • Manage the end-to-end delivery lifecycle for store technology programs, from system integration to testing and deployment
  • Develop strategies for addressing challenges such as system downtime, legacy system integration, and rapid technology scaling
  • Act as a critical nexus between technical, operational, and business teams, driving alignment and streamlined communication across internal stakeholders, external partners, and senior leadership
  • Build trusted relationships with executives, fostering collaboration that ensures consistent program sponsorship and engagement
  • Serve as a mentor and leader to cross-functional teams, building a culture of accountability, innovation, and customer-centricity
  • Define and implement best practices for program delivery, leveraging tools and methodologies such as Agile, Scrum, and Waterfall
  • Continuously monitor and optimize program health with KPIs, risk management strategies, and standardized processes to drive consistent delivery
  • Introduce AI and automation to improve program management, resource allocation, and operational efficiency
  • Keep up-to-date with emerging trends in AI, retail technology, and customer engagement. Actively evaluate opportunities to drive innovation in enterprise applications
  • Develop scalable technology roadmaps to ensure infrastructure remains adaptable to evolving customer and operational needs
Requirements
  • 10+ years of experience leading large-scale, multi-phase program delivery in a technology or retail environment
  • Experience implementing AI-powered solutions, including machine learning models, predictive analytics engines, and intelligent automation
  • Background in store technology delivery, including POS systems, payment platforms, and customer-facing technologies
  • Expertise in cloud-enabled store solutions, system integration, and legacy system compatibility
  • Proficiency in Agile, Scrum, and Waterfall methodologies for program delivery
  • Skills in change management practices to drive technology adoption across organizations
  • Understanding of KPIs, risk management strategies, and standardized processes for program health monitoring
  • Familiarity with emerging trends in AI, retail technology, and customer engagement
  • Capability to build trusted relationships with executives and cross-functional teams
  • Competency in mentoring and leading cross-functional teams to foster accountability, innovation, and customer-centricity