Senior IT Support Specialist

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

Who You Are

• Bachelor’s degree in Computer Science, Information Technology, or a related field — or equivalent practical experience
• 5+ years of IT support experience, including at least 2 years in a senior or L3 support role within a cloud-forward environment
• Advanced troubleshooting skills across both Windows and macOS environments
• Strong experience with identity and access management platforms including Okta, Microsoft Entra ID, and Active Directory
• Hands-on experience managing endpoints with Jamf and Microsoft Intune/Autopilot
• Experience administering enterprise EDR platforms such as CrowdStrike
• Practical scripting experience in PowerShell, Bash, and Python
• Familiarity with AI-assisted support tools and a strong interest in applying AI to IT operations
• Solid networking fundamentals including TCP/IP, DNS, DHCP, SMTP, VPNs, managed switches, and firewalls
• Excellent written and verbal communication skills
• Strong ownership mindset with a track record of improving IT operations and employee experience

Nice to Have:

• Experience with VMware or other virtualization technologies
• Familiarity with ITIL service management practices
• Experience supporting SOC 2 or similar compliance initiatives
• Exposure to AWS and cloud IAM concepts
• Relevant certifications such as:
  • Okta Certified Professional or Administrator
  • Jamf 200/300
  • Microsoft MD-102
  • CompTIA Security+
  • AWS certifications
  • CrowdStrike CCFA