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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.
Job Responsibility:
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
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
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
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
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
Requirements:
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 a fast-paced, complex environment
Nice to have:
Experience in the horse racing industry is very helpful to the success of the role