Support Engineer providing technical assistance to Tailscale's user community by resolving technical issues and maintaining customer support interactions. Join a fully remote team focused on excellent user experiences.
Responsibilities
Act as the primary technical resource for our free user community, resolving a wide range of configuration and networking challenges to keep them unblocked.
Manage a high-velocity ticket queue with a consistent focus on meeting targets for time to first response and time to resolution.
Drive positive user outcomes and maintain high CSAT scores by providing clear, helpful, and accurate technical guidance.
Balance a high volume of daily ticket replies while maintaining the technical depth required to troubleshoot complex networking issues.
Partner cross-functionally to identify recurring friction points and advocate for improvements to the user experience.
Requirements
Bring 1–4+ years of experience in a technical support or customer-facing role, with a track record of solving technical problems.
Display a natural tinkerer’s mindset and a deep curiosity for how things work, likely demonstrated through personal projects, homelabs, or open-source contributions.
Demonstrate a foundational understanding of networking fundamentals, including DNS, IP addressing, firewalls, and routing.
Show proficiency in troubleshooting across multiple operating systems such as macOS, Windows, Linux, and mobile OS’s.
Some familiarity with Jira and Slack to manage internal workflows and communicate effectively with the team and customers.
Exhibit excellent written communication skills, with the ability to explain complex technical concepts with empathy and clarity.
Maintain a proactive approach to learning new technologies and staying current with evolving infra tools.
Benefits
An inclusive, flexible environment where you can be your authentic self.
A competitive total compensation package.
Comprehensive group benefits with no waiting period.
Remote first company—most of our teams work fully remotely.
Connect with other Tailscalars IRL.
Support for your personal and professional development.
Paid time off and a healthy work-life integration.
A build-your-own home office setup.
Generous parental leave program from your first day.
Support specialist ensuring system functionality and user productivity as the first line of technical support. Investigating issues, managing tickets, and provisioning users remotely.
Technical Support Engineer providing escalated technical support for AI platform in insurance claims. Collaborating with cross - functional teams to resolve complex issues and maintain platform configurations.
Technical Support Engineer providing frontline support for enterprise customers in the fleet mobility industry. Collaborating with product teams to resolve complex technical issues and improve product quality.
Technical and Operations Support Agent responsible for managing caisse computer equipment and IT systems in a hybrid work environment. Solution - oriented with a focus on user support, security, and system maintenance.
Remote Technical Support Representative providing technical support via phone and chat. Joining Geek Squad to assist clients across Canada with technology products.
Senior Technical Support Analyst managing large enterprise Cisco networks and providing ongoing IT support for the City of Toronto. Leading technical projects and ensuring system improvements.
IT Technical Support Specialist providing tech support for Varicent's global workforce. Supporting endpoint devices, collaboration tools, and employee technology experience.
Senior Application Support Specialist needed for a contract role in Toronto, ON. Must have Salesforce and SaaS experience, incident management, and customer service skills.
IT Support Developer providing on - site and remote support for IT and network issues across warehouse sites. Involved in cybersecurity, network operation, and pre - sales solution implementation.