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.

Position Overview

Woodbine Entertainment is seeking a visionary and commercially mindedVice 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.

Key Responsibilities

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.

Functional Leadership Areas

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

Qualifications & Experience

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.

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.

Woodbine Entertainment Group remote jobs

Cash Management Analyst

Desktop Analyst

Platform Engineer, Support - 9 Month Contract

Hospitality Attendant

Supervisor, Racing Surfaces

Customer Services Associate

Senior Manager Content Distribution

Host Hostess

Independent Chair Ontario Racing (Independent Contractor Position)

Platform Engineer, Dynamics (F&O)

Driver

Bartender

Licensed Heavy Truck Tech

Starting Gate Driver

Racing Office Clerk

Systems Operation Analyst

Vice President Marketing, Brand Content and Live Experiences

Labourer