TextNow
Senior IT Support Specialist
2w ago
WorldwideSeniorwindowsmacosautomationsecurityidentity management
Senior IT Support Specialist role supporting Windows and macOS environments, driving automation, security, and identity-first initiatives in a cloud-forward organization.
Requirements
- 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
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Other
- 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.
- 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
- 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
- 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
- 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
- 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
- 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
- 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