Senior Microsoft Systems Administrator / Technical Lead

Toronto, ON | Hybrid (3 Days On-Site) | 7+ Years | Day-1 Impact Required The Hook

We are not hiring an administrator. We are poaching a superstar. If you have spent years being the person everyone calls when the setting is on fire, when the migration is going sideways, or when the architecture needs to be rebuilt from the ground up— keep reading. We need a

technical heavyweight

who does not need a 90-day ramp-up. Someone who can

walk in on Day 1, open the hood, understand the environment, and start making it better immediately.

If you are the type of engineer who automates before you are asked, documents before you are required, and leads before you are promoted—we want you. This is not a maintenance role. This is a "come in and own it" role. THE ENVIRONMENT

You will be joining a fast-growing cloud company that manages and operates

business-critical systems —including Enterprise Resource Planning (ERP)—where downtime is not an option, security is non-negotiable, and environments must be predictable, resilient, and highly available. You will be working in a

complex, secure, virtualized, and hybrid cloud infrastructure

that spans on-premises Windows environments, VMware virtualization, and Azure/AWS cloud services. You will be the

highest escalation point

for infrastructure issues, the

architect

for new deployments, and the

mentor

for the next generation of administrators. The environment fosters learning and provides opportunities for growth across

systems, cloud, cybersecurity, and networking.

If you want to expand your skills while solving real, high-stakes problems—this is the place.



CORE INFRASTRUCTURE & VIRTUALIZATION

Windows Server

(2016/2019/2022) Deep expertise: administration, troubleshooting, hardening, performance tuning, and disaster recovery. VMware vSphere / ESXi

Expert-level required.

Design, implementation, troubleshooting, and optimization of virtualized environments. Active Directory

Advanced configuration, Group Policy management, DNS/DHCP, replication troubleshooting, and forest-level design. Remote Desktop Services (RDS)

Design, deployment, and support of multi-session environments. Group Policy

Advanced GPO design, troubleshooting, and security hardening. CLOUD & HYBRID (AZURE / AWS / O365)

Microsoft Azure

IaaS and PaaS deployment, VNet design, VPN Gateway, ExpressRoute, Entra ID (Azure AD), Conditional Access, and hybrid identity. AWS

EC2, S3, VPC, and hybrid connectivity experience.

Strong plus. Microsoft 365 / O365

Administration and troubleshooting: Exchange Online, SharePoint, Teams, Intune. Hybrid Identity

Azure AD Connect, SSO, MFA, and Conditional Access policies. AUTOMATION & SCRIPTING (DO NOT JUST FIX—AUTOMATE)

PowerShell

Advanced scripting.

You should be automating administrative, deployment, and infrastructure tasks without being asked. Infrastructure as Code (IaC)

ARM templates, Bicep, or Terraform. Familiarity is a strong plus. CI/CD Pipelines

Bonus:



Azure DevOps, GitHub Actions, or Jenkins for infrastructure deployment. STORAGE, NETWORKING & SECURITY

SAN Storage

Knowledge of iSCSI, Fibre Channel, NetApp, EMC, or equivalent. Networking

Solid understanding of TCP/IP, routing, switching, firewalls, load balancing, and VLANs. Security

Experience supporting security audits, vulnerability remediation, CIS benchmarks, MFA, and zero-trust principles. BONUS / NICE-TO-HAVE

Linux (Red Hat / Ubuntu) administration. Citrix VDI (XenDesktop / XenApp). ITIL Certification or practical experience with Change Management, Incident Management, and Problem Management. Microsoft Certifications (Azure Administrator, Azure Solutions Architect, VMware VCP, etc.) — strong plus. KEY RESPONSIBILITIES (WHAT YOU WILL DO FROM DAY 1)

ARCHITECTURE & DESIGN

Evaluate, architect, and implement secure, high-availability server and web service environments. Design and execute migration strategies (on-prem to cloud, cloud to cloud, legacy modernization) with minimal downtime and zero data loss. Provide technical recommendations based on industry best practices, security audits, and business requirements. Anticipate and research new cloud and web technologies appropriate to our infrastructure, platform, and products. OPERATIONS & ESCALATION

Serve as the highest level of escalation for complex infrastructure issues. You are the person the team calls when they are stuck. Perform advanced server setup, administration, and configuration across Windows and virtualized environments. Troubleshoot and resolve problems quickly and effectively—and communicate clearly with pe

📌 SENIOR MICROSOFT SYSTEMS ADMINISTRATOR (Winnipeg)
🏢 Logic Hire Solutions
📍 Winnipeg