Windows System Administrator

1 week ago

Toronto, Ontario, Canada Idea Theorem™ Full time $80,000 - $120,000 per year

Position Type:
Contract – Support & Maintenance Engagement

Location:
Hybrid – Primarily remote with occasional on-site collaboration in Toronto, ON

Duration:
January 2026 – December 2027 (with option to renew)

Reports to:
Technical Lead / Project Manager

Position Overview

The Windows System Administrator will be responsible for administering, maintaining, and supporting on-premise or hybrid infrastructure environments hosting enterprise .NET applications.

This role ensures system availability, stability, and security across all Windows Server and IIS environments in alignment with organizational IT standards.

Key Responsibilities

  • Administer and maintain Microsoft Windows Server 2016 Standard environments supporting IIS 10.
  • Manage IIS sites, application pools, SSL certificates, bindings, and configurations.
  • Coordinate and perform system patching, updates, and backups.
  • Monitor system performance (CPU, memory, disk utilization, uptime), investigate incidents, and apply corrective actions.
  • Implement and maintain security policies, firewall configurations, and access controls.
  • Troubleshoot network connectivity and TCP/IP-related issues affecting hosted applications.
  • Support deployments of .NET applications (v2.0–4.5) in coordination with developers and DBAs.
  • Maintain operational documentation including change logs, configuration guides, and recovery procedures.
  • Collaborate with internal IT teams and vendors to plan upgrades or maintenance windows.
  • Participate in contingency planning to ensure minimal downtime for business-critical systems.

Required Skills and Experience

  • 5+ years of experience administering Windows Server 2012–2019 (Server 2016 mandatory).
  • Proficiency with IIS 10, PowerShell scripting, and system automation.
  • Strong understanding of network protocols (TCP/IP, DNS, DHCP, VPN).
  • Experience with Active Directory and user access management.
  • Experience supporting applications built in ASP.NET (VB and C#).
  • Excellent documentation, troubleshooting, and communication skills.
  • Ability to coordinate remotely and occasionally attend client offices.

Preferred Assets

  • Microsoft Certified: Windows Server Administrator or Azure Administrator.
  • Experience with Azure services and hybrid integrations.
  • Knowledge of DevOps and CI/CD pipelines (Azure DevOps, GitHub Actions).
  • Previous experience in enterprise or regulated environments.

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