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We’re looking for a Senior IT Support Specialist to join our IT team in Waterloo. In this role, you’ll act as a senior technical resource supporting both Windows and macOS environments while helping drive automation, security, and identity-first initiatives across a modern, cloud-forward organization.

You’ll collaborate closely with IT, Security, Engineering, and People Operations teams to resolve escalations, lead projects, and continuously improve the employee technology experience.

This is a hybrid role based in our Waterloo office. You'll be in the office a minimum of 3 days a week, including Wednesdays.

What You’ll Do

End-User Support & Escalations

Serve as a senior escalation point for complex issues across Windows and macOS endpoints, networking, identity systems, and enterprise SaaS applications
Resolve escalated tickets end-to-end while maintaining clear communication with employees and stakeholders
Participate in the IT on-call rotation, including after-hours support for business-critical incidents
Mentor and support other IT team members through coaching, documentation, and knowledge sharing

Identity & Access Management

Administer identity and access management platforms including Okta and Microsoft Entra ID within a hybrid Active Directory environment
Support joiner, mover, and leaver workflows, access reviews, group policies, and conditional access policies
Improve identity automation and provisioning processes to reduce manual effort and improve operational efficiency

Endpoint Management

Manage macOS devices through Jamf and Windows devices through Microsoft Intune and Autopilot
Support zero-touch provisioning, configuration management, patching, and compliance enforcement
Maintain secure deployment standards, hardening baselines, and operating system upgrade cycles

Security Operations

Operate endpoint security tooling, including agent health monitoring, policy tuning, and alert triage in collaboration with the Security team
Enforce IT security best practices around endpoint compliance, least-privilege access, patch management, data protection, and offboarding
Support compliance and audit initiatives through accurate asset tracking, access reviews, and change documentation

Automation, Scripting & AI

Build and maintain automation workflows using PowerShell, Bash, and Python
Contribute to AI-assisted IT support experiences and internal knowledge systems
Identify repetitive operational tasks and improve them through scripting, integrations, and AI-driven solutions

Infrastructure & Enterprise Systems

Support office networking infrastructure including managed switches, VPN, Wi-Fi, and firewalls
Administer enterprise platforms including Microsoft 365, SharePoint, Jira, Confluence, and Slack
Provide support for VMware-based virtualization environments as needed

Projects & Documentation

Lead IT projects from planning through rollout, including pilots, stakeholder coordination, and execution
Create and maintain high-quality technical documentation, runbooks, and troubleshooting guides
Conduct risk assessments and follow established change-management practices