Woodbine Entertainment is seeking a visionary and commercially minded Vice President, Marketing, Brand Content & Live Experiences to lead the development and execution of integrated brand, content, customer experience, and live event strategies that drive audience growth, engagement, and revenue.

Reporting to the Executive Vice President, Revenue, Brand & Experience, the Vice President will be a strategic and creative leader responsible for building, elevating, and rejuvenating Woodbine Entertainment’s brands while creating compelling customer experiences that attract new audiences and deepen engagement with racing, wagering, entertainment, dining, and hospitality offerings.

This leader will champion innovation, transformation, and customer-centric thinking across the organization. As a key member of the leadership team, the Vice President will contribute to the execution of the corporate strategic plan and achievement of long-term business, operational, and financial objectives.

Brand Strategy & Commercial Growth

• Provide strategic leadership that drives top-line revenue growth and strengthens brand equity.

• Lead the development and execution of marketing strategies that support corporate objectives, business performance, and customer acquisition.

• Develop long-term growth strategies for key customer segments and oversee an integrated commercial planning process.

• Lead the evolution of Woodbine’s digital customer engagement strategy, leveraging digital platforms, content, and data to expand audiences, strengthen fan relationships, and drive measurable commercial outcomes.

• Establish performance measures, track key performance indicators (KPIs), and optimize programs based on ROI and business outcomes.

• Align cross-functional stakeholders around brand strategy, business priorities, and commercial objectives.

• Manage departmental budgets, annual operating plans, and resource allocation to ensure effective execution.

Brand Development & Creative Leadership

• Lead the strategy and execution of initiatives that build, elevate, and rejuvenate Woodbine Entertainment’s portfolio of brands.

• Champion brand standards and oversee all creative development across physical, broadcast, digital, social, and experiential channels.

• Ensure consistent and compelling brand storytelling that strengthens customer awareness and engagement.

• Guide creative teams and agency partners to deliver high-impact campaigns and customer communications.

Live Experiences, Events & Customer Experience

• Oversee the planning, development, and execution of major events and customer activations, including marquee events such as the King’s Plate.

• Lead the strategy and delivery of customer-centric experiences across racing, food and beverage, hospitality, and special events.

• Develop initiatives designed to attract new audiences, increase visitation, and drive engagement with racing and wagering products.

• Lead enterprise-wide customer experience (CX) strategy, including customer journey mapping, measurement, analytics, insights, and service design.

• Oversee property-wide branding, sponsorship commitments, development initiatives, and onsite communication strategies.

Content, Broadcast & Media

• Lead the vision, strategy, and execution of Woodbine’s multi-platform content ecosystem.

• Oversee content creation and distribution across video, editorial, social media, email, influencer partnerships, and other owned and partner channels.

• Drive content strategies that accelerate customer acquisition, strengthen fan development, and drive wagering growth, with a strong focus on delivering compelling racing and betting content that deepens engagement and loyalty among both new and existing customers

• Lead the development and execution of Woodbine’s broadcast products, including nationally distributed racing content and innovative television programming that expands the sport’s reach and relevance.

• Ensure the effective delivery of world-class live simulcast production and broadcast operations.

Leadership & Organizational Development

• Lead, coach, and inspire a high-performing team of more than 50 employees, including three Director-level direct reports.

• Foster a customer-centric, collaborative, and results-oriented culture.

• Build organizational capability through effective talent development, succession planning, coaching, and performance management.

• Lead transformational initiatives and champion innovation throughout the organization.

The Vice President will oversee five primary areas of responsibility:

1. Brand & Creative Development

• Brand strategy and positioning

• Creative development and advertising

• Social media and digital communications

• In-venue branding and customer communications

• Broadcast creative integration

2. In-Venue Experience Strategy & Design

• Customer experience strategy and measurement

• Food & beverage experience development

• Experience innovation and service design

• Customer journey optimization

3. Events & Activations

• Signature events, including the King’s Plate

• Customer engagement programs

• Corporate and group experiences

• Sponsorship activations and partnerships

4. Broadcast Development & Production

• National television programming

• Live racing broadcast production

• Simulcast operations

• New media and broadcast growth initiatives

5. Content Strategy

• Content planning and production

• Editorial and storytelling strategy

• Video and social content creation

• Distribution through owned and partner channels

Required Experience

• 15+ years of progressive leadership experience in consumer marketing, brand management, customer experience, media, content, entertainment, sports, hospitality, retail, or related industries.

• Progressive experience in consumer marketing and brand leadership, with a proven track record of building, elevating, and rejuvenating brands through integrated marketing and communications strategies. Experience across content, customer experience, and live experiences, complemented by strong expertise in consumer marketing and brand management.

• Proven success developing and executing strategic business plans that drive revenue growth and brand performance.

• Demonstrated expertise across brand management, customer acquisition, customer segmentation, digital marketing, content strategy, social media, and customer experience.

• Strong commercial acumen with experience managing budgets, performance metrics, and business planning.

• Experience leading large, multi-disciplinary teams and fostering high-performance cultures.

• Strategic and hands-on leadership approach, with a demonstrated ability to translate long-term strategy into disciplined, effective execution within complex, fast-paced operating environments

Education

• Undergraduate degree in Business, Marketing, Communications, or a related field.

• MBA or other advanced business education is considered an asset.

Working Conditions

• Hybrid work environment with an expectation of three days per week onsite and two days remote.

• Regular attendance at live racing, entertainment events, and customer-facing experiences, including evenings, weekends, and holidays as required.

• Occasional travel within the Greater Toronto Area, including Woodbine Racetrack and Woodbine Mohawk Park located outside of Milton.

Reason for Vacancy: Replacement

We use AI-powered resume screening software to help identify qualified candidates based on the criteria in this job posting. All applications prioritized by the system are subsequently reviewed by our hiring team to ensure a fair and human-centered selection process

Why Join Woodbine Entertainment?

This is a unique opportunity to shape the future of one of Canada’s most iconic sport entertainment brands. The Vice President, Brand, Content & Live Experiences will play a pivotal role in growing audiences, advancing customer engagement, elevating the brand, and creating memorable experiences that connect new generations of fans to the excitement of horse racing.