Jobs at Woodbine Entertainment Group

Monitors surveillance cameras, alarms, and access controls in a 24/7 security operations center. Investigates criminal activity, racing integrity issues, employee security breaches, and incidents; prepares defensible reports and video evidence; coordinates responses with security staff, management, regulators, police, and emergency personnel; supports special events and risk assessments; and provides court testimony when required.

Supports product roadmaps, requirements gathering, prioritization, stakeholder engagement, technology-enabled solution delivery, vendor coordination, and continuous product improvement. Coordinates small to medium-sized initiatives, monitors product adoption and business outcomes, and contributes to project budgets, CapEx tracking, invoice validation, and funding forecasts. Serves as a bridge between business teams, technology teams, and external partners to deliver measurable business value.

Provides friendly, professional customer service to Woodbine Entertainment guests, addresses product and service needs, and accurately processes transactions using OLG lottery terminals and point-of-sale systems. The role requires effective communication, basic math skills, cash-handling knowledge, adherence to appearance standards, and availability for afternoon, evening, and weekend shifts in a fast-paced entertainment environment.

The Independent Chair provides strategic leadership to Ontario Racing, chairs Board meetings, builds consensus, manages relationships across the horse racing industry, and advocates with government and public-sector partners. The role supports long-term industry priorities, governance, accountability, innovation, and stakeholder engagement. Candidates need deep Ontario horse racing knowledge, substantial senior leadership experience, strong communication and consensus-building skills, government relations expertise, and an independent perspective free from conflicts of interest.

Maintain and enhance the Microsoft Dynamics 365 Finance and Operations platform by designing customizations, resolving defects, developing integrations, and improving business processes. Analyze requirements, document software specifications, plan SDLC activities, coordinate upgrades, and identify solutions using out-of-the-box functionality. Collaborate with technical teams to resolve system issues and provide guidance to junior developers. Align business requirements with platform capabilities and Microsoft release plans.

Provides technical support, troubleshooting, maintenance, and development for applications, databases, ETL workflows, APIs, and internal websites. Responsibilities include database optimization, monitoring, preventive maintenance, QA, user support, documentation, reporting, data integration, JavaScript automation, and DevOps improvements. Collaborates with stakeholders and developers to resolve issues, enhance reliability, prevent fraud, and automate processes.

Supervise and manage daily maintenance of the Standardbred racing surface at Woodbine Mohawk Park, lead a 10–15 person crew, ensure equipment operability and safety, create work schedules and track logs, evaluate track conditions and recommend race cancellations, and maintain relationships with horsemen and racing staff.