Jobs at Woodbine Entertainment Group

Leads integrated brand, content, customer experience, live event, broadcast, and marketing strategies to grow audiences, engagement, revenue, and brand equity. Oversees digital engagement, creative development, events, customer journeys, sponsorships, broadcast programming, content distribution, budgets, and performance metrics. Manages a multidisciplinary team of more than 50 employees, develops organizational capability, and drives transformational initiatives across racing, wagering, dining, hospitality, and entertainment experiences.

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.

Design, develop and maintain ETL workflows, SQL stored procedures, databases and integrations. Monitor and QA systems, create alerts, automate tests (JavaScript APIs), produce reports/dashboards, document processes, and provide user support while applying DevOps practices to improve system reliability and performance.

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.

Senior-level infrastructure analyst responsible for monitoring, troubleshooting, and maintaining core network routing, perimeter firewalls, multi-cloud environments (Azure/AWS/GCP), virtualization and HCI platforms, and enterprise endpoint services using Microsoft 365 and Intune. Acts as Tier 3 escalation for service desk, automates tasks with PowerShell/Bash/Python, and supports cross-team operational priorities.

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.

Perform general maintenance and manual labour across facilities, grounds, tracks and stables: landscaping, turf care, snow removal, cleaning, minor repairs, equipment upkeep, emergency response, and assist other trades to maintain a safe, clean venue.