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

Salary Range:

138,400.00 - 188,400.00 CAD

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

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.

YOUR ROLE IN THE GAME

Reporting to the Sr Director IT Workforce Enablement, you will be empowered to:

• 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.

WHAT YOU BRING TO THE GAME

Education & Experience:

• 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

Relevant Skills:

Behaviors

• Collaboration: Leads and influences diverse stakeholders to build strong partnerships, drive alignment, and achieve shared organizational outcomes.
• Improvement Mindset: Champions continuous improvement by driving initiatives that enhance organizational effectiveness and align with strategic objectives.
• Problem Solving: Anticipates complex challenges and opportunities, developing strategic solutions that support organizational goals and priorities.

Ways of Working

• Works confidently in ambiguity, connecting the dots across complex inputs and translating conceptual direction into practical, actionable plans.
• Considers different lenses and stakeholder perspectives to shape solutions that are thoughtful, balanced, and aligned to enterprise priorities.
• Moves with pace and agility by testing, learning, iterating, and adjusting as priorities, information, and organizational needs evolve.
• Demonstrates a proactive, go-getter mindset by stepping in when needs or opportunities emerge and leading through influence across a broad range of stakeholders.

Empowerment Factors

• Autonomy: Exercises significant decision-making authority and accountability within a major area of responsibility, guiding strategic and operational outcomes.
• Complexity: Leads highly complex initiatives involving multiple technical, operational, financial, and organizational considerations.
• Influence: Shapes strategy, drives organizational alignment, and influences key decisions through strong leadership and stakeholder engagement.

BENEFITS OF JOINING THE WINNING TEAM

• 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.

To learn more about our organization and other opportunities visit our career site.

We look forward to hearing from you, interested applicants please apply online by July 28, 2026.

Please Note: Unless otherwise specified, all positions are required to work fully onsite.

OLG is an equal opportunity employer. We are committed to providing employment accommodation in accordance with the Ontario Human Rights Code and the Accessibility for Ontarians with Disabilities Act. Please contact Human Resources at [email protected] if you require accommodation at any time throughout the hire process.

We welcome applicants from all backgrounds and experiences. If you bring relevant skills and a willingness to learn, we encourage you to apply—even if you don’t meet every listed qualification. We sincerely appreciate your interest; while we are unable to contact everyone, those selected for the next steps will be notified.

We thank you for your interest in this opportunity; however only those individuals selected for an interview will be contacted.

Personal information is collected by the Ontario Lottery & Gaming Corporation (OLG) and/or its third party service provider(s) under the authority of the Ontario Lottery and Gaming Corporation Act, 1999, SO 1999, c 12, Sch L and the Employment Standards Act, 2000, S.O. 2000, c. 41 (as amended) and will be used for the purpose of determining qualifications for employment with OLG and for recruitment modernization initiatives. The information will be managed in accordance with all applicable laws, OLG’s Protection of Privacy Policy (the Policy) and related policies and procedures. For any questions about this collection, please contact [email protected], 800-70 Foster Drive, Sault Ste. Marie, ON, P6A 6V2.