About UJA Federation of Greater Toronto:

At UJA Federation of Greater Toronto, our vision is to lead the most vibrant Jewish community in North America - a community characterized by its diversity, unity, compassion, generosity and commitment to Jewish values. Together with our philanthropic, volunteer and professional leadership, we’re changing lives.

As one of North America’s leading Jewish non-profits, UJA Federation of Greater Toronto works to preserve and strengthen the quality of Jewish life in Greater Toronto, Canada, Israel and around the world. UJA advances this mission through fundraising, programs, and research focused on our strategic pillars: fighting poverty and improving well-being, growing Jewish education and identity, countering antisemitism and hate, and strengthening connections with Israel and Jewish communities worldwide.

About the Opportunity:

We 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 strong root-cause-analysis instincts, a service-oriented mindset, and the ability to lead end users through AI-powered change.

Responsibilities include, but are not limited to:

Infrastructure & Virtualization

• Manage a large-scale server virtualization environment (50+ VMs) supporting mission-critical business systems, ensuring high availability, performance, and capacity planning.
• Administer Windows and Linux Server environments including Active Directory, Group Policy, DNS, DHCP, DFS, RDS, WDS, and Certificate Services.
• Implement and maintain enterprise backup and disaster recovery solutions, ensuring business continuity, tested recovery objectives, and data protection compliance.
• Perform troubleshooting and diagnostics for servers, desktops, laptops, and peripherals across multi-site locations.

Microsoft 365 & Identity

• Administer Microsoft 365 across multiple tenants including Exchange Online, Teams, SharePoint, Intune, Entra ID, and Microsoft 365 Copilot.
• Manage cloud identity and access, including multi-factor authentication, conditional access policies, and privileged identity governance.
• Lead onboarding of new business units and partner agencies including Microsoft 365 provisioning, device management, MFA enrollment, and network access setup.

AI, Copilot & Emerging Technology

• Lead the enterprise-wide rollout of Microsoft 365 Copilot, including licensing governance, tenant configuration, data access controls, Sensitivity Labels, and DLP policy alignment to ensure a secure and responsible deployment.
• Design and deliver end-user Copilot training programs, adoption playbooks, and department-specific use-case guides to drive measurable productivity gains across the organization.
• Evaluate and implement AI-powered IT operations tools to improve monitoring, incident detection, and automated remediation across infrastructure platforms.
• Maintain awareness of Microsoft’s AI roadmap (Copilot Studio, Azure AI, Power Platform AI) and advise leadership on adoption sequencing, risk, and business value.

Networking & Security

• Maintain enterprise network infrastructure across multiple sites including managed switches, VLANs, TCP/IP routing, and VPN connectivity.
• Administer enterprise next-generation firewall platforms in high-availability configurations, enforcing security policies, network segmentation, and zero-trust principles.
• Implement and manage enterprise email security solutions including anti-phishing, anti-spoofing, and advanced threat protection capabilities.
• Design and maintain segmented network infrastructure for physical security systems including VLAN routing and perimeter policy enforcement.

Operations, Support & Projects

• Serve as the senior technical escalation point (L2–L3) for infrastructure, network, and Microsoft 365 incidents across a large multi-site user base, maintaining high system uptime.
• Perform structured root cause analysis to resolve complex infrastructure, network, and cloud platform issues, preventing recurrence through permanent remediation.
• Lead large-scale infrastructure migrations and technology refresh projects end-to-end, from scoping and vendor coordination through implementation, testing, and handover.
• Develop and maintain documentation, standard operating procedures (SOPs), and system configurations aligned with SLAs, change management processes, and audit requirements.
• Collaborate with vendors on technology deployments, manage hardware lifecycles, and evaluate competitive solutions aligned to organizational needs and budget.
• Develop scripting and automation solutions (PowerShell and equivalent) for provisioning, reporting, and routine administrative task reduction.

Required Qualifications

• 5+ years of progressive experience supporting enterprise IT infrastructure in complex, multi-site organizations with large user populations.
• Hands-on experience administering enterprise server virtualization platforms at scale (50+ VMs), including VM lifecycle management, HA clustering, and performance tuning.
• Deep, hands-on expertise with Windows Server administration including Active Directory, Group Policy, DNS, DHCP, RDS, DFS, and Certificate Services.
• Strong working knowledge of Microsoft 365 administration including Exchange Online, Teams, SharePoint, Intune, and Entra ID, ideally across multiple tenants.
• Demonstrated experience planning or leading a Microsoft 365 Copilot deployment, including data governance readiness, licensing strategy, and end-user enablement.
• Solid networking fundamentals: TCP/IP, VLANs, routing, VPN, and enterprise switch administration across mixed-vendor environments.
• Production experience with enterprise next-generation firewalls, including high-availability cluster configurations, security policy management, and network segmentation.
• Experience designing and operating enterprise backup and disaster recovery platforms, with a track record of tested and validated recovery objectives.
• Working scripting ability (PowerShell or equivalent) for automation, provisioning, and reporting.
• Experience leading enterprise infrastructure projects end-to-end — scoping, vendor coordination, implementation, documentation, and handover.
• Post-secondary education in Computer Systems Technology, Computer Science, or equivalent practical experience.
• Excellent troubleshooting, documentation, and stakeholder communication skills.

Preferred Qualifications

• Microsoft 365 certifications (e.g., Microsoft 365 Certified: Administrator Expert, Endpoint Administrator, or Security Administrator Associate).
• Microsoft AI or Copilot credentials, such as Azure AI Fundamentals (AI-900), Microsoft Applied Skills in Copilot, or equivalent hands-on Copilot Studio / AI Builder experience.
• Security certifications such as CompTIA Security+, Microsoft SC-200 (Security Operations Analyst), or equivalent.
• ITIL v4 Foundation certification or demonstrated ITSM process experience.
• Experience designing and delivering technology training programs, adoption workshops, or lunch-and-learns for non-technical end users and department leads.
• Familiarity with AI governance frameworks, responsible AI principles, and data privacy considerations relevant to deploying AI tools in a regulated or non-profit environment.
• Experience supporting multi-tenant Microsoft 365 environments or multi-site organizations.
• Exposure to enterprise network monitoring and ITSM platforms for event management, capacity reporting, and service desk integration.
• Familiarity with enterprise email security platforms, cloud-managed switching, VoIP systems, SAN/NAS storage, and physical security infrastructure (CCTV/access control).
  

* 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).

We look forward to connecting with you to understanding what you can bring to the UJA team and how we can support your career goals. Qualified applicants are invited to submit a cover letter and resume. Only those applicants invited for interview will be contacted. 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 Accessibility:

UJA 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.