Job Description

A NEW BREED OF ENTERTAINMENT

With almost 150 years of proud horseracing history, Woodbine Entertainment Group is the founding pioneer and largest operator of professional horseracing in Canada.

Building on our rich past, we are surging ahead to the future with an energized, new vision. Today we deliver the most thrilling and highest quality racing, dining and entertainment experiences to our visitors. In doing so, we remain a world-leader in horse-racing — and also among the most exciting and diverse entertainment facilities on the globe.

The Senior Manager, Wagering Development & Strategy is responsible for leading the development, execution, and ongoing evolution of Woodbine’s wagering growth strategy. Reporting into senior leadership, this role provides strategic direction and oversight for wagering initiatives across products, platforms, partnerships, and channels, ensuring alignment with Woodbine’s long-term business objectives.

This role owns the wagering strategic roadmap, translates enterprise goals into actionable initiatives, and ensures disciplined execution across multiple, concurrent programs. The Senior Manager serves as a subject-matter expert and strategic partner to internal teams and external stakeholders, driving innovation, optimizing performance, and identifying new accretive wagering opportunities. This position plays a critical role in shaping the future of wagering at Woodbine through data-driven decision-making, market insight, and strong cross-functional leadership.

Responsibilities

Wagering Strategy & Roadmap Leadership

• Own and lead the multi-year wagering development and strategic roadmap, ensuring alignment with enterprise objectives and long-term growth priorities.
• Translate corporate strategy into a sequenced pipeline of wagering initiatives, balancing innovation, risk, and return.

New Wagering Product & NPI Leadership

• Provide strategic leadership over the end-to-end wagering product and platform lifecycle, from concept through launch and optimization.
• Own the Wagering Development New Initiative process, ensuring initiatives are rigorously evaluated, prioritized, and governed.
• Lead the development of robust financial, operational, and customer-impact business cases for new wagering products, platform enhancements, and channel innovations.
• Partner cross-functionally to ensure initiatives are delivered on time, on budget, and against defined success metrics.

Market Assessment & Opportunity Discovery

• Conduct ongoing market, competitive, and customer assessments to identify emerging trends, unmet needs, and whitespace opportunities within wagering.
• Evaluate the commercial viability of new wagering concepts using data-driven analysis, scenario modeling, and market insights.
• Proactively surface and shape new growth opportunities, presenting clear recommendations supported by evidence and financial rigor.
• Monitor global and local wagering developments to inform future strategy and mitigate potential threats.

Performance Management & Strategic Governance

• Establish and oversee KPIs, reporting frameworks, and governance processes for wagering initiatives.
• Track progress, manage risks, and ensure accountability across the wagering development portfolio.
• Provide concise, actionable updates to senior leadership on performance, risks, and strategic implications.

Leadership & Capability Development

• Provide direct leadership and strategic direction to the wagering development team.
• Act as an internal consultant and subject-matter expert, supporting decision-making across the organization.
• Foster a culture of analytical rigor, innovation, and continuous improvement.

Qualifications

• University degree in Business Administration, Strategy, Finance, Marketing, or a related discipline.
• Extensive hands-on experience leading wagering, gaming, or digital product initiatives in a regulated industry.
• Post-graduate education (MBA or equivalent) is considered a strong asset.
• Demonstrated expertise in business case development, including financial modeling, ROI analysis, and scenario planning.
• Strong consultative skill set, with the ability to diagnose business challenges, frame strategic options, and influence senior decision-makers.
• Proven knowledge of New Initiative Introduction frameworks and pipeline management, including stage-gate governance and prioritization.
• Deep understanding of wagering ecosystems, digital platforms, customer experience design, and regulated operating environments.
• Formal training or applied experience in strategy development, product management, or program leadership is preferred.

Reason for Vacancy: New position

Salary range: $100,000 to $115,000 per year

Diversity, Equity, Inclusion and Belonging

Be Yourself.

We believe differences should be valued and celebrated. By building diverse and inclusive teams, we strive to provide a more authentic and empowering work experience that unlocks the potential of our people. Regardless of race, religion, colour, national origin, sex, gender, expression, sexual orientation, age, marital status, veteran status, or disability status, we believe everyone has the right to express their ideas, ambitions, and pursue their goals with confidence and integrity. Diversity breeds innovation. We want people to think differently. Our commitment is to build a culture that welcomes everyone and leverages their unique perspectives to be a great entertainment company that shares the thrill of horseracing experiences with the world.