Senior Systems Administrator

Job summary

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.

Job details

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.

What you’ll do

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.

Benefits

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

Listed skills

• Active Directory · Preferred
• VMware · Preferred

Other relevant skills

Identified from the job description. Confirm important requirements above.

• 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

Job areas

• Technology
• Security & Safety
• Management & Leadership
• Finance & Accounting