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. Job Summary The Manager, IT Operations is a strategic and technical leader responsible for ensuring the reliability, security, and efficiency of the organization’s IT infrastructure. This role oversees day-to-day operations across servers, networks, and hybrid cloud environments, applying ITIL-based frameworks for incident, problem, and change management. The manager enforces rigorous security and compliance standards, manages budgets and vendor relationships, and leads a high-performing team to deliver exceptional technology services. Additionally, this position drives process and architectural improvements, fosters collaboration with cross-functional teams, and maintains clear communication with senior leadership to align IT operations with strategic business objectives. Key Responsibilities Manage daily operations across on-premises, network infrastructure, and hybrid cloud environments. Apply ITIL-based frameworks for incident, problem, and change management to ensure structured and effective service delivery. Proactively identify and implement process and architectural improvements to enhance operational excellence and scalability. Manage departmental budgets effectively and cultivate strong relationships with key technology vendors. Foster strong collaboration with cross-functional teams and maintain clear communication with senior leadership to align IT operations with strategic business objectives. Lead the design, maintenance, and optimization of complex infrastructure environments, including virtualization platforms, storage systems, and network architecture. Utilize advanced proficiency in Microsoft Active Directory, domain architecture, Group Policy management, PowerShell scripting, and enterprise-level Microsoft licensing. Implement robust cloud integration strategies, identity and access management (IAM) protocols, and security hardening techniques across multi-platform environments. Leverage automation tools, comprehensive monitoring solutions, and performance optimization methodologies to ensure system resilience and efficiency. Lead, mentor, and develop a high-performing team of technical professionals, fostering accountability and innovation. Implement structured development plans to enhance technical depth and certifications, guiding staff in advanced system administration, security best practices, and emerging technologies. Accountable for achieving and reporting on key performance indicators (KPIs), including maintaining 99.5%+ system uptime for critical infrastructure and achieving 85–90% incident resolution within defined Service Level Agreements (SLAs). Qualifications Bachelor’s degree in Computer Science, Information Technology, or a related field (Master’s degree is a plus) 5–7 years of IT experience, with at least 2+ years in a supervisory or management role Proven experience managing IT infrastructure (servers, networks, storage, cloud environments) This role involves managing critical IT infrastructure and services that directly impact business continuity. It requires balancing operational stability, security, and efficiency Multi-Domain Knowledge: Must handle networking, servers, storage, cloud platforms, and security compliance simultaneously Cross-Functional Coordination: Requires collaboration with application teams, security, and business stakeholders Problem-Solving Under Pressure: Must resolve incidents quickly to minimize downtime and maintain SLAs 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. At the core of everything we do is the beauty of the race horse, but it takes thousands of people from diverse backgrounds to do it as well as we do. Our team is expanding, and we want to hire the most talented people we can. Our team members work in fields such as wagering, hospitality, marketing, property services, finance, broadcasting, IT and much more. Once you've had a chance to explore our current open positions, apply to the ones you feel suit you best and keep track of both your progress in the selection process, and new postings that might interest you! Thanks for your interest in working with Woodbine Entertainment! With almost 150 years of proud horseracing history, Woodbine Entertainment 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.
