Senior IT Support Specialist

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.  

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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

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

The expected base salary range for this role is: 

CAD $85,000 - $122,000 annually 

Our salary ranges are determined by role, level, and location. Within the range, individual pay is determined by job-related skills, experience, and relevant education or training. 

Our goal is to offer a competitive package that reflects the impact and expertise you bring to the team. 

This posting is for a current, active vacancy.

More about TextNow  

Our culture  

We’re proud of the culture that we’ve built at TextNow, but one of the most common questions we hear is ‘how do you continue to sustain it as the world and the company continues to change?’ The reality is that we’re only able to keep up because each and every TextNovian contributes to our culture through being involved, by living our values, sharing feedback, embracing change and more!  

Our values  

Customer Obsessed  

We strive to have a deep understanding of our customers. 

Do Right By Our People  

We treat each other with fairness, respect, and integrity. 

Accept the Challenge  

We adopt a "Yes, We Can" mindset to achieve ambitious goals. 

Act Like an Owner  

We treat this company like it's our own... because it is! 

Give a Damn  

We are deeply committed and passionate about our work and achieving results. 

Our benefits and more  

This is a brief overview of the benefits that TextNow offers its employees. More complete details can be found in TextNow’s Benefit Guide and legal plan documents, which are available to employees on or shortly after their start date with TextNow. The benefits listed herein are for illustrative purposes only and may change from time-to-time in TextNow’s sole discretion. 

Free phone service 

Strong work life blend  

Flexible work arrangements (work-from-home, remote, or access to one of our office spaces) 

Employee stock options  

Unlimited vacation  

12 paid holidays per year 

Competitive pay 

Health, dental, and vision benefits 

Short-term & long-term disability 

$750 annual wellness benefit or healthcare spending account 

RRSP matching (Canada)

Parental leave for eligible employees 

Learning & Development opportunities

We travel a few times a year for various team events, company-wide off-sites, and more 

More information about our total rewards package will be available during the hiring process. 

Dogfooding & Customer Obsession  

At TextNow, every employee gets to actively use our app for calling and texting. Dogfooding helps us experience what customers do, to spot issues early, and drive better design, developer, and user experiences. 

Diversity and Inclusion  

Our aim is to make every person who joins TextNow feel like they belong, that they’re valued, and that they’re able to be their authentic selves at work.  

We’re all accountable for creating an inclusive culture and a sense of belonging for one another. By doing this together, we’ll make TextNow better for everyone.  

Equal opportunity  

We are an equal opportunity employer and are committed to creating an inclusive environment for all employees. We consider all qualified applicants without regard to race, color, religion, sex, gender identity or expression, sexual orientation, age, disability, or any other protected characteristic. 

Applicants who require reasonable accommodation during the hiring process may contact our Talent Team. 

AI usage: We use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact our Talent Team.

TextNow Candidate Policy  

By submitting an application to TextNow, you agree to the collection, use, and disclosure of your personal information in accordance with the TextNow Candidate Policy