Customer Support Engineer

Tailscale

Support Engineer solving complex technical issues for Tailscale customers in a remote capacity. Part of a distributed team focused on delivering excellent customer support.

Posted 6/26/2026full-timeRemote • 🇨🇦 CanadaMid-LevelSenior💰 CA$129,980 - CA$162,140 per yearWebsite

Tech Stack

Tools & technologies

DNSFirewallsKubernetesLinuxMacOSTCP/IP

About the role

Key responsibilities & impact

Serve as the primary escalation point for technically complex tickets raised by paying customers.
Diagnose and troubleshoot advanced Tailscale-specific issues.
Manage a ticket queue with a consistent focus on SLA adherence.
Drive positive user outcomes and maintain high CSAT scores.
Balance a high volume of daily ticket replies while maintaining the technical depth.
Partner cross-functionally to identify recurring friction points.
Own escalations of technically complex tickets from Tier 1.
Mentor and support Tier 1 colleagues through ticket reviews.

Requirements

What you’ll need

4+ years of experience in a technical support role within a SaaS company.
Hands-on familiarity with Tailscale or comparable networking/VPN products strongly preferred.
Display a natural tinkerer’s mindset and a deep curiosity for how things work.
Strong working knowledge of networking fundamentals - TCP/IP, DNS, subnetting, firewalls, NAT traversal, and routing.
Show proficiency in troubleshooting across multiple operating systems such as macOS, Windows, Linux, and mobile platforms.
Experience working with identity providers and SSO integrations.
Basic experience troubleshooting Kubernetes environments.
Familiarity with log analysis and CLI-based diagnostic tools.

Benefits

Comp & perks

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.

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

troubleshootingnetworking fundamentalsTCP/IPDNSsubnettingfirewallsNAT traversalroutingKuberneteslog analysis

Soft Skills

mentoringproblem-solvingcommunicationcollaborationcustomer servicetime managementcuriosityadaptabilityattention to detailSLA adherence