Systems Operation Analyst

Woodbine Entertainment • Etobicoke, ON

2d • CA$90,000 - CA$105,000

About The Position

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.

Requirements

• Minimum 5+ years of deep, hands-on engineering experience spanning advanced network administration, cloud infrastructure engineering, and enterprise-scale desktop management.
• Advanced technical expertise in configuring, optimizing, and maintaining core networking protocols, enterprise perimeter firewalls, and hybrid cloud network routing fabrics.
• 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.
• 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.
• Demonstrated experience serving as a Tier 3 escalation engineer, resolving deep-seated, systemic infrastructure failures within a structured Service Desk or TSC environment.
• Proficiency in architecting and deploying production-grade PowerShell, Bash, or Python scripts to automate complex infrastructure provisioning, system configurations, or routine administrative routines.

Responsibilities

• Monitoring, troubleshooting, and maintaining performance across core network routing, perimeter firewalls, and multi-platform cloud ecosystems, including Azure, AWS, and GCP.
• Ensuring the stability and optimization of advanced virtual machine environments, spanning traditional hypervisors and modern Hyper-Converged Infrastructure (HCI).
• Serving 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.
• Acting as a vital escalation point for the Technical Support Center (TSC) team, taking ownership of deep, complex technical issues.
• Actively helping to upskill frontline analysts.
• Supporting multiple internal infrastructure and project teams as operational priorities shift.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed