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Added 13 mins ago
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HEB MANITOBA

Senior Systems Administrator

Winnipeg, MB, Canada

Job type: Full-time
Apply by: Mar 31, 2027
Experience: Minimum 7 years of progressive experience administering enterprise infrastructure.
Posting language: English
Posted: Oct 2, 2026

Apply About employer

Applications open in a new tab.

Original job description

Help us serve over 100,000 of Manitoba’s healthcare professionals. We are HEB Manitoba, one of the largest pension and benefit plans in the province.

The Information Services Department supports HEB Manitoba’s strategic objectives by developing and maintaining a robust technology environment that ensures high-quality service delivery to members and stakeholders.

Reporting to the Manager, Information Technology Services, the Senior Systems Administrator is HEB Manitoba's senior technical resource for infrastructure, cloud, and security operations, maintaining the environments that support service delivery to over 100,000 healthcare professionals across Manitoba.

The role is the escalation point for complex incidents, a mentor to the Technical Support Specialist team, and a hands-on contributor to HEB's technology modernization agenda. It operates within a regulated environment governed by Manitoba PHIA, FIPPA, and applicable pension and benefits legislation.

If you are an experienced technology professional who enjoys solving complex problems, working across multiple technical disciplines, and influencing how systems evolve, this is an opportunity to make a visible and lasting contribution.

Follow this path to personal growth and challenges in your new career:

In the first three months with us, you will:

Learn about HEB Manitoba's services and how technology supports our members and employers.
Build relationships with the Information Services team while becoming familiar with our technology environment, operational practices, and service delivery processes.
Begin contributing to operational activities, modernization initiatives, and continuous improvement opportunities.

Over the first year, your responsibilities will increase as you settle into your new role. You will:

Administer and optimize HEB's server, storage, network, and virtualization environments, including maintenance outside business hours as required.
Administer Microsoft 365 services, including Entra ID, Intune, Exchange Online, SharePoint Online, and Teams, and supports endpoint lifecycle through Autopilot and Group Policy.
Monitor system health and capacity to resolve issues before they affect service.
Execute vulnerability and patch management and support cyber incident response with the ISPO team, in compliance with PHIA and FIPPA.
Lead the technical assessment of HEB's VMware environment and support the remediation roadmap, including Hyper-V and cloud options.
Lead initiatives that improve automation, standardization, performance, security, and operational efficiency.
Evaluate technologies and recommend solutions that align with HEB Manitoba's architecture, operational requirements, and long-term technology direction.
Follow change and release management practices and maintains knowledge articles, diagrams, and procedures

Qualifications for Your Success:

Education & Experience

Post-secondary degree or diploma in Computer Science, Information Technology, or a related discipline, or an equivalent combination of education and experience.
Minimum 7 years of progressive experience administering enterprise infrastructure.
Demonstrated experience with Microsoft 365, Entra ID, Intune, VMware, and Hyper-V, and with on-premises to cloud migrations.
Experience in regulated or data-intensive environments such as pension, benefits, healthcare, or financial services is a strong asset.
Microsoft, cloud, virtualization, networking, or security certifications and experience with IT service management (ITSM) practices are considered a strong asset.

Other Competencies, Knowledge & Skills

Advanced knowledge of Windows Server, Active Directory, hybrid identity, DNS, DHCP, and Group Policy.
Working knowledge of enterprise networking, including firewalls, switching, routing, and VPN.
Strong understanding of cybersecurity, backup, and disaster recovery; JIRA Service Management experience is an asset.
Advanced troubleshooting and analytical skills with sound judgment under pressure.
Excellent written and verbal communication, including explaining technical matters to non-technical audiences and mentoring colleagues.
Proven ability to balance operational and project priorities, with discretion in handling confidential information.
Ability to work effectively with cross-functional groups.

Why join our team?

The work you do will be challenging and rewarding. You will make a difference in our day-to-day operations and your initiative will be appreciated.

We offer:

Hybrid work environment with a compressed work week for your work/life balance.
Comprehensive compensation and benefits including a defined benefit pension plan.
Professional development opportunities.
Progressive and supportive work environment.
A comfortable, modern environment conveniently located in downtown Winnipeg with easy access to shopping and restaurants.

Please submit your resume and cover letter by 4:00 p.m. on Wednesday October 14, 2026 to hr@hebmanitoba.ca.

Apply About employer

More about this job

Responsibilities

Administer and optimize enterprise infrastructure, Microsoft 365 services, virtualization, and cloud environments while monitoring system health and managing vulnerabilities, patches, and incident response. Lead infrastructure modernization and operational improvement initiatives, evaluate technology solutions, and maintain technical documentation while mentoring support staff.

Requirements

Requires a post-secondary degree or diploma in Computer Science, Information Technology, or a related discipline, or equivalent education and experience, plus at least seven years of progressive enterprise infrastructure administration experience. Candidates should have experience with Microsoft 365, Entra ID, Intune, VMware, Hyper-V, and cloud migrations, along with strong Windows Server, networking, cybersecurity, troubleshooting, communication, and mentoring skills.

Skills

Windows Server Administration
Microsoft 365 Administration
Entra ID
Intune
VMware
Hyper-V
Active Directory
Hybrid Identity
Enterprise Networking
Vulnerability Management
Patch Management
Cybersecurity
Backup and Disaster Recovery
Cloud Migration
Automation
Advanced Troubleshooting

Benefits

Defined Benefit Pension Plan
Professional Development Opportunities
Hybrid Work Environment
Compressed Work Week

Visa sponsorship

Not detected in the job text

Keywords

Windows Server
Active Directory
Microsoft 365
Entra ID
Intune
Exchange Online
SharePoint Online
Microsoft Teams
Autopilot
Group Policy
VMware
Hyper-V
Cloud Migration
Enterprise Infrastructure
Server Administration
Storage
Virtualization
Enterprise Networking
Firewalls
Switching
Routing
VPN
Vulnerability Management
Patch Management
Cyber Incident Response
Backup and Disaster Recovery
PHIA
FIPPA
IT Service Management
JIRA Service Management

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