Overview

Our client is seeking a hands-on IT Generalist for a 2-month contract based in Winnipeg, MB, requiring 35 hours per week and 100% onsite presence. The successful candidate will step into a well-established environment to provide continuity during a leadership transition and ensure the stability of day-to-day IT operations.

This role is best suited for a seasoned IT professional who is comfortable working across infrastructure, systems administration, networking, security, and end-user support. You will support a hybrid environment consisting of Azure cloud services, approximately 30 servers, and on-premises Hyper-V infrastructure, while ensuring reliable and secure technology services for approximately 150 users across Canada.

The focus of this engagement is maintaining operational excellence, managing service requests, supporting ongoing security improvements, and contributing to business continuity and disaster recovery initiatives. This is not a major transformation role; rather, the successful candidate will provide hands-on technical leadership and help keep critical IT systems running smoothly during the transition period.

Key Responsibilities

• Provide day-to-day operational leadership and support to a small IT team.
• Manage and support a Microsoft 365 environment, including Azure AD/Entra ID, Exchange Online, Teams, SharePoint, and related services.
• Maintain and administer a hybrid infrastructure consisting of Azure cloud services and on-premises Hyper-V environments.
• Support approximately 30 servers across cloud and on-premises environments.
• Oversee user provisioning, access management, system monitoring, and troubleshooting activities.
• Manage and process IT service requests through the organization's ticketing platform.
• Assist with ongoing cybersecurity initiatives, remediation efforts, and security best practices.
• Support incident response, backup management, and business continuity/disaster recovery activities.
• Evaluate and implement approved change requests while ensuring minimal disruption to business operations.
• Collaborate with business stakeholders to understand technology requirements and support operational improvements.
• Ensure reliable, secure, and efficient IT services for approximately 150 users located across Canada.
• Maintain documentation, procedures, and technical standards.

Required Qualifications

• 7+ years of hands-on IT infrastructure and operations experience.
• Previous experience leading projects, mentoring staff, or providing team oversight.
• Strong Microsoft 365 administration experience, including Azure AD / Entra ID, Exchange Online, Microsoft Teams, SharePoint Online and Intune
• Experience supporting hybrid cloud environments utilizing Azure and on-premises infrastructure.
• Strong Windows Server administration experience.
• Experience with virtualization technologies, preferably Hyper-V.
• Knowledge of networking concepts including switching, routing, VPNs, firewalls, and connectivity troubleshooting.
• Experience supporting cybersecurity initiatives, vulnerability remediation, and security best practices.
• Familiarity with backup, recovery, and disaster recovery planning.
• Strong troubleshooting and communication skills with the ability to work independently.

Nice to Have

• Experience in a standalone or senior IT generalist capacity.
• Security certifications such as CISSP, Security+, or related credentials.
• Experience reviewing business requirements and translating them into technical solutions.
• Previous experience working in a multi-site environment.

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