Job Description
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. The Systems Analyst – Core Technology Team is an advanced, specialized technical role requiring an exceptional range of skills across modern endpoints, public cloud infrastructure, advanced virtualization, and core networking. Reporting directly to the Senior Manager, IT Operations, this position is built for a highly capable technician who possesses deep expertise across distinct technical domains, allowing them to seamlessly manage and troubleshoot everything from desktop software packages to complex network routing and public cloud fabrics. This individual provides a high-level technical range to the operations department. They must be an agile problem-solver who thinks quickly on their feet, possesses strong technical stamina, and is eager to jump in and support multiple internal infrastructure and project teams as operational priorities shift. Additionally, this position serves as a vital escalation point for the Technical Support Center (TSC) team, taking ownership of deep, complex technical issues and actively helping to upskill frontline analysts. Key responsibilities include monitoring, troubleshooting, and maintaining performance across core network routing, perimeter firewalls, and multi-platform cloud ecosystems, including Azure, AWS, and GCP. The role is deeply focused on ensuring the stability and optimization of advanced virtual machine environments, spanning traditional hypervisors and modern Hyper-Converged Infrastructure (HCI). Additionally, the analyst serves as the primary technical engine for modern workplace services, leveraging Microsoft Intune and the full Microsoft 365 suite to manage silent application packaging, device compliance, and multi-OS enterprise endpoint lifecycles.
