Senior Microsoft Systems Administrator

Senior Microsoft Systems Administrator / Technical Lead
Toronto, ON | Hybrid (3 Days On-Site) | 7+ Years | Day-1 Impact RequiredThe Hook
We are not hiring an administrator. We are poaching a superstar.If you have spent years being the person everyone calls when the environment 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 peers and end-user clients during troubleshooting, planning, and migration.Perform server and application deployments, configurations, updates, and improvements.Support functionality and security audits and provide technical recommendations to harden the environment.AUTOMATION & PROCESS IMPROVEMENT
Develop scripts (PowerShell) to automate common administrative, deployment, and infrastructure tasks.Help define, improve, document, and promote architecture and designs based on ITIL "best practices."Create and maintain clear documentation of processes and work being done.Demonstrate ability to create processes and document work being done—not just do the work.LEADERSHIP & COLLABORATION
Mentor junior team members and share knowledge across the team.Develop relationships with professional organizations, user groups, and industry trade groups to stay current with the latest technologies.Collaborate with cross-functional global teams to ensure seamless delivery of services.ON-CALL
Willingness to participate in a 7/24 on-call rotation to respond to and resolve systems and application issues to ensure we meet or exceed committed service level agreements (SLAs).MUST-HAVE QUALIFICATIONS
RequirementDetailEducation
Degree in Information Technology, Engineering, or equivalent experience.Overall Experience
7+ years of experience in IT infrastructure, with a heavy focus on systems administration and engineering.Virtualization
5+ years of experience in virtualized technology infrastructure design, implementation, and troubleshooting.Windows Systems
5+ years of experience operating Windows Systems Administration and troubleshooting.Domain Expertise
Expert domain knowledge and proven experience in at least one of the following areas: Active Directory, Azure, VMware, Remote Desktop Services, or Windows Servers.Availability
Willingness to participate in a 7/24 on-call rotation.SOFT SKILLS (THE "SUPERSTAR" FACTOR)
We are looking for someone who is not just technically brilliant but also a great fit for a collaborative, fast-paced, high-stakes team.Customer Focus
Excellent customer interaction with strong written and verbal communication skills. You can explain complex technical concepts to non-technical stakeholders.Organization
Strong organizational skills and the ability to track and prioritize several tasks simultaneously.Autonomy
Demonstrate teamwork skills, plus the ability to work
without direct supervision.Problem Solving
Excellent problem-solving skills, along with the ability to work independently and as part of a cross-functional global team.Documentation
Demonstrated ability to create processes and document work being done.Networking & Security
Basic knowledge of networking and security concepts (though your deeper expertise will be in systems).WHY THIS ROLE IS DIFFERENT
You will not be bored. This is a high-availability, business-critical environment. The problems are real, the stakes are high, and the solutions matter.You will not be micromanaged. We expect you to crack on from Day 1. We hire superstars and trust them to lead.You will grow. The environment fosters learning and provides opportunities for growth across systems, cloud, cybersecurity, and networking.You will be valued. We are a team of motivated individuals with a strong customer focus who make a difference every day. We recognize and reward technical excellence.Hybrid Flexibility: Enjoy the balance of 3 days on-site in our Toronto office for collaboration and 2 days remote for focused work.THE BOTTOM LINE
Skills: infrastructure,security,windows,server admin,azure,cloud,vmware certified professional
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