We believe communication belongs to everyone. We exist to democratize phone service. TextNow is evolving the way the world connects and that's because we're made up of people with curious minds who bring an optimistic, yet critical lens into the work we do.

We're the largest provider of free phone service in the nation. And we're just getting started. Join us in our mission to break down barriers to communication and free the flow of conversation for people everywhere.

*]:pointer-events-auto R6Vx5W_threadScrollVars scroll-mb-[calc(var(--scroll-root-safe-area-inset-bottom,0px)+var(--thread-response-height))] scroll-mt-[calc(var(--header-height)+min(200px,max(70px,20svh)))]" data-turn-id="request-WEB:6e47135b-914e-4f92-b5d9-bc7f074e16ee-1" data-turn-id-container="request-WEB:6e47135b-914e-4f92-b5d9-bc7f074e16ee-1" data-testid="conversation-turn-4" data-scroll-anchor="false" data-turn="assistant"> 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.

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 equivale