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Website: tailscale.com
Tailscale Inc. is a software company based in Toronto, Ontario. Tailscale develops an open-source software-defined mesh virtual private network (VPN) and a web-based management service. The company provides a zero config VPN as a service under the same name.
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Tailscale is recruiting a full-time Customer Support Engineer for a remote position based in the United Kingdom, where you will provide advanced technical assistance to users of all sizes. What This Role Involves This Tier 2 Customer Support Engineer opportunity places you at the forefront of customer interactions for teams relying on Tailscale, addressing a wide spectrum of technical enquiries that demand both depth and clarity. You join a fully distributed support group reporting to the Support Team Lead, collaborating routinely with customer experience, product and engineering colleagues to eliminate pain points before they escalate. The work revolves around ownership of sophisticated cases drawn from both free and paying users while upholding excellence in response quality and user confidence. Responsibilities Serve as the principal escalation contact for intricate technical tickets submitted by paying customers and retain full ownership until each is resolved. Examine and correct advanced Tailscale configuration difficulties such as access-control-list errors, subnet routing, exit-node setups and identity-provider integrations including Okta and Azure AD. Administer an active case queue while prioritising adherence to service-level agreements through swift initial replies and thorough closures. Secure favourable user results and elevated satisfaction ratings by furnishing accurate, understandable technical direction. Sustain a high daily volume of ticket answers while preserving the analytical expertise needed for complex networking problems. Work across functions to surface recurring friction and champion enhancements that improve the overall user experience. Assume responsibility for escalations received from Tier 1, encompassing free-tier submissions that exceed first-line capability, and drive them to efficient conclusion. Coach Tier 1 colleagues through constructive ticket reviews, escalation advice and contributions to shared documentation. Skills & Qualifications Four or more years of technical support experience inside a SaaS organisation, including proven handling of escalated or enterprise-level accounts. Practical exposure to Tailscale itself or comparable networking and virtual-private-network technologies (such as WireGuard or conventional VPNs) is strongly preferred. A natural experimenter’s outlook and deep curiosity about system behaviour, typically evidenced by personal projects, home laboratories or open-source participation. Confident command of networking essentials—TCP/IP, DNS, subnetting, firewalls, NAT traversal and routing—together with the skill to apply them in live…
Generated for personal interview prep · 2026-07-17 UTC · getajob.ai