Job Description
Overview
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.
Woodbine Entertainment is looking for a 12-month Maternity Leave replacement for the Director of Brand and Live Experience. Reporting to the Vice President of Brand, Content & Live Experience, the Director Brand and Live Experience will lead and inspire a high-performing team to execute customer-centric strategies for onsite wagering, live horse racing events, and the overall guest experience at both racetracks.
This Leader Owns The Guest Experience For
Our high impact events like King’s Plate, Greenwood Stakes, North American Cup, and more. Our everyday experiences at the track like wagering engagement, VIP Player development and dining. Innovative and effective marketing campaigns to drive guests to the track. This role oversees a team of 10, with 4 direct reports comprised of the Brand, Live Experiences, Creative Services (in-house agency), and digital web & email teams.
Key Responsibilities
Lead the planning and execution of marquee racing events and major onsite activations
Ensure exceptional guest experience, strong wagering engagement, and sponsor fulfillment
Drive attendance, wagering, and brand impact through flawless delivery
Everyday Experiences, Player Engagement & Acquisition
Oversee VIP Player Development Experiences, Race Day Engagement, and Customer Acquisition initiatives
Optimize non-event race days to increase visitation, dwell time, and wagering behaviour
Ensure consistency and quality across all onsite experiences
Integrated Brand, Marketing & Promotion Strategy
Lead integrated marketing efforts promoting racing, events, and hospitality
Direct Creative, Digital, Web, Email, and CRM teams to deliver measurable revenue growth
Elevate horse racing and Woodbine’s facilities as premium entertainment destinations
Team Leadership & Operational Excellence
Lead, coach, and manage a high-performing team across Brand, Live Experience, Creative, and Digital
Set clear priorities, allocate resources, and ensure timely, high-quality execution
Foster collaboration, accountability, and a strong performance culture
Stakeholder Alignment, Sponsorship & Governance
Deliver against sponsorship commitments through integrated onsite and marketing execution
Partner cross-functionally with Racing, Wagering, Hospitality, and Operations teams
Provide clear reporting, risk management, and executive updates
Qualifications
10+ years of experience in event management, planning & execution, preferably in sports & entertainment
University or college degree/diploma in Business Administration, Marketing, Sponsorships or related fields
Expert understanding of marketing strategy
Expert understanding of promotion and advertising – both media and creative
Demonstrated ability to bring cross-functional groups together, set objectives and achieve goals without direct reporting authority
Advanced understanding of budgeting, financial management and resource allocation
Advanced organizational skills to manage varying demands, time constraints and direct reports
Advanced negotiation skills for negotiating external supplier contracts
Experience in the horse racing industry is very helpful to the success of the role
Experience in a fast-paced, complex environment
Reason for vacancy: Replacement
Salary range: $120,000 to $130,000 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.
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