Jobs at Woodbine Entertainment Group

Provides friendly, proactive service to horseracing and wagering customers. Responsibilities include explaining betting options, assisting with wagering terminals and accounts, selling racing programs, OLG products, merchandise, and game rentals, maintaining promotional displays, reconciling sales, replenishing wagering equipment, educating customers on promotions, and supporting marketing events.

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.

Provide friendly, professional guest service; address product and service needs; accurately process transactions using OLG lottery terminals and POS; handle cash/tendering, perform basic calculations, communicate in English, maintain company appearance standards; work afternoon/evening shifts including weekends.

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.

Provide end-user technical support for hardware, software, and connectivity via onsite visits and remote sessions. Install, configure, troubleshoot, repair, maintain, and upgrade devices; document issues and follow standard procedures; coordinate with external vendors and advise users on effective technology use.