About the OpportunityWe are seeking a seasoned Senior Systems Engineer to take ownership of our enterprise IT infrastructure — spanning server virtualization, Windows and cloud environments, Microsoft 365, networking, security platforms, and AI productivity tooling. Reporting to the IT Operations Manager, you will be the technical anchor for a large, multi‑site user base, ensuring that mission‑critical systems remain highly available, secure, and well‑documented — while also spearheading the organization’s adoption of Microsoft Copilot and AI‑powered capabilities.This is a hands‑on senior individual contributor role with significant project leadership scope. You will lead infrastructure upgrades, drive cloud and security initiatives, champion the Microsoft Copilot rollout, and serve as the senior escalation point across the organization. The ideal candidate combines deep technical expertise across enterprise virtualization, Windows Server, and Microsoft 365 with robust root‑cause‑analysis instincts, a service‑oriented mindset, and the ability to lead end users through AI‑powered change.Key ResponsibilitiesInfrastructure & SystemsAdminister enterprise virtualization (50+ VMs), Windows and Linux servers, Active Directory, Group Policy, DNS, DHCP, DFS, RDS, WDS, and Certificate Services.Manage backup, disaster recovery, system performance, capacity planning, and business continuity.Troubleshoot infrastructure, endpoints, and peripherals across multiple locations.Microsoft 365 & AIManage identity, MFA, Conditional Access, and privileged access.Lead Microsoft Copilot deployment, governance, licensing, data protection, training, and user adoption.Evaluate emerging AI technologies and recommend solutions that improve productivity and IT operations.Networking & SecurityMaintain enterprise networking, VLANs, routing, VPNs, and switching.Administer next‑generation firewalls, email security,



network segmentation, and Zero Trust security practices.Support physical security network infrastructure.Projects & OperationsAct as the senior L2/L3 escalation resource.Lead infrastructure upgrades, cloud migrations, and technology refresh projects.Perform root cause analysis and implement permanent solutions.Develop documentation, SOPs, automation scripts (PowerShell), and collaborate with vendors on technology initiatives.5+ years supporting enterprise IT infrastructure in complex, multi‑site environments.Experience administering enterprise virtualization (50+ VMs).Strong Windows Server expertise, including Active Directory, Group Policy, DNS, DHCP, DFS, RDS, and Certificate Services.Experience administering Microsoft 365, Exchange Online, Teams, SharePoint, Intune, and Entra ID.Experience planning or supporting Microsoft 365 Copilot deployments.Strong networking knowledge (TCP/IP, VLANs, routing, VPNs, switching).Experience with enterprise firewalls, backup and disaster recovery, and PowerShell scripting.Proven experience leading enterprise infrastructure projects.Postsecondary education in Computer Systems Technology, Computer Science, or equivalent experience.Strong troubleshooting, documentation, and communication skills.Preferred QualificationsMicrosoft 365, Microsoft AI/Copilot, Security+, SC‑200, or ITIL certifications.Experience delivering technology training and driving user adoption.Knowledge of AI governance, responsible AI practices,



and data privacy.Experience supporting multi‑tenant Microsoft 365 environments, enterprise monitoring tools, VoIP, SAN/NAS storage, email security, and physical security systems.* This is a full‑time 12 month contract position. Salary Range: $80,000–$90,000 annually, based on experience. At UJA we support a flexible work schedule and all of our employees engage in hybrid work. Engagement and connection are key to supporting the best employee experience and we want to ensure that this puts balance and well‑being at the forefront of our approach to ways of working. In addition to a rich time off policy, UJA’s offices are closed on all Jewish holy days (yom tov) and we support early office closures to observe the Jewish Sabbath (Shabbat).Please be advised that all offers of employment are contingent upon the successful completion of professional references and background checks including Social Media Account(s) and a Police Records Check/Vulnerable Sector Screening.Commitment to Inclusion and AccessibilityUJA Federation supports a diverse candidate and employment experience. We are proud of our dynamic professional team, which reflects the diversity of the Jewish community and general community alike in Greater Toronto. We are an equal opportunity employer and welcome applicants from all communities. We encourage you to follow us to get regular updates on open roles. We are committed to creating an inclusive and accessible workplace and believe this is essential to ensure that every member of our team can thrive.We adhere to barrier‑free and accessible employment practices in compliance with the Accessibility for Ontarians with Disabilities Act (AODA). Should you require Code‑protected accommodation through any stage of the recruitment process, please notify us and we will work with you to meet your needs.#J-18808-Ljbffr

📌 Senior Systems Engineer(12 Month Contract) - $80,000 - $90,000 A Year (Winnipeg)
🏢 UJA Federation
📍 Winnipeg