Senior IT Systems Administrator

The Descartes•Waterloo, ON

8d•CA$90,000 - CA$100,000•Remote

About The Position

As a Senior IT Administrator (Remote, Replacement Role), you will ensure the stability, scalability, and evolution of Descartes’ global cloud and hybrid infrastructure. This role exists to maintain continuity in a mature environment while accelerating our transition toward modern, automated, and cloud-first operations that directly support business performance and resilience.

Requirements

Deep expertise in managing large-scale cloud and hybrid IT environments (Azure, Microsoft 365, Windows Server)
Strong analytical thinking and advanced troubleshooting skills applied to complex, distributed systems
Proven ability to lead technical initiatives and influence decisions across global, remote teams
Proficiency in automation (PowerShell, Azure CLI) and Infrastructure as Code (IaC) practices
Ability to design, document, and communicate scalable cloud architectures clearly
Strong collaboration skills with both technical and non-technical stakeholders

Responsibilities

Maintain >99.9% uptime across critical hybrid (cloud/on-prem) infrastructure while reducing incident resolution times by 20% within 12 months
Successfully lead and deliver key Azure and Microsoft 365 migration/modernization initiatives on time and within scope
Increase infrastructure automation coverage (IaC, scripting) by at least 40% within 18 months
Improve security posture and compliance across cloud and on-prem systems, with measurable reductions in vulnerabilities and audit findings
Establish and document scalable, standardized architectures for hybrid environments adopted across global teams
Enhance monitoring, alerting, and incident response processes to proactively identify and resolve issues before business impact
Actively contribute to and influence cloud strategy through technical recommendations adopted by leadership