VP Lottery Strategy, Transformation, & Customer Experience

OLG • Toronto, ON

6d • Onsite

About The Position

We are ready to take this game to the next level and need someone passionate about leading the strategic evolution and transformation of OLG's Lottery business. As VP, Lottery Strategy, Transformation & Enterprise Customer Experience, you will provide executive leadership for Lottery strategy, business transformation, planning and performance, and enterprise customer experience. This role will drive the delivery of large-scale business and technology initiatives, champion a customer-centric and data-driven culture and ensure the Lottery division is positioned for long-term growth, operational excellence, and sustainable value creation. As a member of the Lottery Senior Leadership Team, you will play a critical role in shaping the future of the business and driving alignment across the division and the broader organization. You will also serve as a key strategic advisor, influencing priorities, executive decision-making, and the long-term direction of one of OLG's largest lines of business.

Requirements

• University degree in Business, Commerce, Finance, Technology, Marketing, Strategy, or a related field.
• Significant executive leadership experience developing and executing business strategy within complex organizations.
• Demonstrated experience leading large-scale business and technology transformation programs, including governance, business case ownership, change management, and benefits realization.
• Experience leading multi-year enterprise transformation programs involving technology modernization, operating model redesign, organizational change, and business readiness activities.
• Experience building and managing portfolios of strategic initiatives and translating strategy into measurable business outcomes.
• Experience establishing and leading business performance management frameworks including KPIs, OKRs, forecasting, and executive reporting processes.
• Experience leading enterprise customer experience, consumer insights, or customer research functions.
• Experience developing and implementing enterprise customer experience strategies, frameworks, and voice-of-customer programs across multiple business functions.
• Experience developing go-to-market strategies and driving successful customer adoption of new products, services, technology platforms, or business capabilities.
• Experience operating within highly regulated industries such as gaming, lottery, financial services, or similar environments.
• Proven experience leading cross-functional teams and influencing senior stakeholders across large, complex organizations.
• Exceptional strategic thinking, business acumen, and commercial judgment.
• Strong understanding of organizational transformation, operating model design, and change leadership.
• Experience leveraging analytics, performance metrics, and business insights to drive decision-making and results.
• Ability to effectively partner with Technology, Data & Analytics, Cybersecurity, and Architecture teams to deliver innovative and scalable solutions.
• Strong knowledge of risk management, governance, regulatory compliance, privacy, and audit requirements.
• Outstanding communication, influencing, negotiation, and stakeholder management skills.
• Demonstrated ability to build alignment across diverse stakeholder groups, including executives, business leaders, vendors, and external partners.
• Demonstrated ability to lead large-scale organizational change across geographically dispersed teams, customer-facing operations, and partner networks.
• Proven ability to lead through ambiguity, manage competing priorities, and drive results in a dynamic environment.
• Passion for innovation, customer experience, continuous improvement, and organizational excellence.

Nice To Haves

• Graduate degree (MBA or equivalent) and/or relevant professional designation(s) considered an asset.

Responsibilities

• Lead the strategic direction, transformation roadmap, and operating model evolution of OLG's Lottery business, integrating technology delivery, organizational design, business processes, and change management to ensure alignment with business objectives, organizational readiness, and sustainable value creation.
• Provide executive sponsorship and governance for large-scale transformation initiatives, overseeing business case management, benefits realization, risks, dependencies, and delivery outcomes.
• Ensure the Lottery business is operationally, commercially, and financially prepared for transformational change, maintaining accountability for business case integrity and long-term value realization.
• Lead and align the Transformation, Strategy, Planning & Performance, and Enterprise Customer Experience teams to achieve business priorities and deliver measurable results.
• Develop and execute the multi-year Lottery strategy, translating long-term objectives into actionable priorities, initiatives, and performance measures.
• Oversee the Lottery portfolio of strategic initiatives, ensuring effective prioritization, resource allocation, business alignment, and execution.
• Shape and govern the strategic initiative portfolio by identifying, evaluating, and prioritizing opportunities based on business value, strategic fit, organizational capacity, and long-term growth objectives.
• Lead business planning, performance management, forecasting, and reporting activities, using data and analytics to support informed decision-making and continuous improvement.
• Lead the Planning & Performance function in establishing the operating rhythm for the Lottery division, including annual planning cycles, OKR management, forecasting, executive reporting, performance reviews, and ongoing business performance monitoring.
• Establish and monitor key performance indicators to measure transformation progress, operational performance, customer adoption, organizational readiness, and value realization.
• Champion a customer-centric and data-driven culture by leveraging customer insights, voice-of-the-customer programs, and performance analytics to inform strategy and business outcomes.
• Lead OLG's Enterprise Customer Experience function, serving as the organization's centre of excellence for customer experience programs, frameworks, standards, and voice-of-the-customer initiatives across lines of business while providing dedicated customer insight, research, and advisory services to the Lottery division.
• Drive change management and adoption across OLG's retail network and internal teams, ensuring stakeholders are engaged, prepared, and successful in adopting new technologies, processes, and ways of working.
• Lead go-to-market strategies for major Lottery initiatives, including new products, technology platforms, and hardware introductions, partnering with Marketing, Product, and Retail Distribution teams to drive customer adoption, commercial performance, and market success.
• Partner with Technology, Data & Analytics, Cybersecurity, Enterprise Architecture, and other enterprise functions to deliver secure, scalable, and innovative solutions.
• Ensure compliance with regulatory, privacy, audit, responsible gaming, and governance requirements while maintaining strong operational controls and risk management practices.
• Build and sustain a high-performing leadership team and culture, fostering collaboration, accountability, talent development, and organizational effectiveness.

Benefits

• Eligible employees and dependents have access to comprehensive, employer-paid group benefits coverage (permanent employees only).
• Participation in a highly desirable defined benefit pension plan.
• Participation in a performance-based incentive plan that recognizes organizational and individual achievements (permanent employees only).
• Competitive paid time-off provisions to support work-life balance and well-being.
• Become your best self with access to new opportunities and personalized support programs.
• 24/7 access to robust online learning programs.
• 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: Executive