Systems Operation Analyst

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.

Qualifications:

• Minimum 5+ years of deep, hands-on engineering experience spanning advanced network administration, cloud infrastructure engineering, and enterprise-scale desktop management.

• Networking & Firewalls: Advanced technical expertise in configuring, optimizing, and maintaining core networking protocols, enterprise perimeter firewalls, and hybrid cloud network routing fabrics.

• Cloud & Virtualization: Proven track record ensuring the seamless scaling, stability, and administration of enterprise virtualization layers (VMs, host clusters, HCI platforms) alongside public cloud architectures within Azure, AWS, or GCP.

• M365 & MDM: Extensive, deep technical command over the comprehensive Microsoft 365 ecosystem and Microsoft Intune to orchestrate advanced software packaging, rigorous device compliance baselines, and complex multi-OS enterprise endpoint lifecycles.

• Escalation Support: Demonstrated experience serving as a Tier 3 escalation engineer, resolving deep-seated, systemic infrastructure failures within a structured Service Desk or TSC environment.

• Automation: Proficiency in architecting and deploying production-grade PowerShell, Bash, or Python scripts to automate complex infrastructure provisioning, system configurations, or routine administrative routines.

Reason for Vacancy: New Position

Salary: The target hiring salary range for this position is $90,000 - $105,000. This range is not a guarantee of compensation. Final placement within the range depends on factors such as internal equity, market conditions, and the candidate’s experience, skills, and qualifications relevant to the role.

We use AI-powered resume screening software to help identify qualified candidates based on the criteria in this job posting. All applications prioritized by the system are subsequently reviewed by our hiring team to ensure a fair and human-centered selection process

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.