Senior IT Systems Administrator

The DescartesWaterloo, ON
CA$90,000 - CA$100,000Remote

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

Benefits

  • competitive compensation
  • great benefits
  • remote and flexible work hours
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