Enterprise IT Transformation & Organizational Readiness Director (18-month contract)

OLG • Toronto, ON

1d • CA$138,400 - CA$188,400 • Onsite

About The Position

We are ready to take this game to the next level and need someone passionate to lead enterprise-wide workforce planning and organizational change efforts that enable EIT to adapt to evolving priorities. They drive the design and execution of change strategies, ensuring the organization is equipped with the skills, capabilities, behaviors, and structures needed for successful transformation that meet business priorities.

Requirements

• Degree in Information Technology, Business, or a related discipline.
• Strong understanding of IT operating models, agile and DevOps ways of working, and digital transformation practices.
• Deep knowledge of organizational change management and capability development in a technology-driven environment.
• 7–10 years’ progressive experience in transformation roles involving workforce planning or organizational change within IT or technology-driven environments.
• Proven track record of leading enterprise change initiatives and aligning talent strategies with agile and digital ways of working.
• Experience collaborating with cross-functional teams, senior leaders, and technical stakeholders to drive capability development and organizational readiness.

Nice To Haves

• If you bring relevant skills and a willingness to learn, we encourage you to apply—even if you don’t meet every listed qualification.

Responsibilities

• Lead Organizational Transformation by designing organizational structures, operating models, and accountability frameworks that align EIT's capabilities with strategic business priorities.
• Drive Transformation Governance by establishing nimble, yet structured, executive decision forums, and transformation roadmaps that connect strategy to execution and ensure outcomes are measured and realized.
• Execute Operating Model Change by translating future-state designs into practical implementation plans and guiding teams through phased transformation efforts.
• Improve Organizational Effectiveness by identifying organizational barriers, optimizing team effectiveness, and implementing solutions that enhance efficiency, decision-making, and delivery outcomes.
• Lead Organizational Readiness & Adoption by supporting leaders and teams through change, building adoption strategies, and helping sustain new behaviors and ways of working.
• Strengthen Strategic Partnerships by collaborating with EIT leaders, People & Culture, and key stakeholders to build organizational capability, leadership effectiveness, and workforce adaptability.
• Champion AI-Enabled Optimization by identifying opportunities to leverage AI and emerging technologies to improve productivity, streamline work, and enhance organizational performance.
• Foster Continuous Improvement by promoting a culture of innovation, collaboration, adaptability, and learning that prepares EIT for future business and technology needs.
• Bridge Strategy and Execution by turning transformational vision into actionable plans, governance mechanisms, operating models, and measurable outcomes, while maintaining accountability through implementation and adoption.

Benefits

• Group Benefits Plan: Eligible employees and dependents have access to comprehensive, employer-paid group benefits coverage (permanent employees only).
• Public Service Pension Plan: Participation in a highly desirable defined benefit pension plan.
• Variable Pay Program: Participation in a performance-based incentive plan that recognizes organizational and individual achievements (permanent employees only).
• Paid Time-Off: Competitive paid time-off provisions to support work-life balance and well-being.
• Growth Focus: Become your best self with access to new opportunities and personalized support programs.
• Comprehensive Learning: 24/7 access to robust online learning programs.
• Equity, diversity, and inclusion: Core to OLG’s culture, empowering employees to bring their authentic selves and make a meaningful impact across Ontario.

What This Job Offers

• Job Type: Full-time
• Career Level: Director