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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 hiring a full-time Senior Customer Support Engineer (Tier 3), Customer Escalations for a remote role based in the United Kingdom. This opportunity suits technical specialists who excel at resolving the most complex customer challenges while creating clear pathways to engineering solutions. The Opportunity As fully remote Senior Customer Support Engineer (Tier 3), Customer Escalations at Tailscale you will take ownership of highly complex and unclear escalations arising after sale. Work each case through to completion or prepare a fully actionable open package so engineering can begin immediately. The role reports to the Customer Escalations Team Lead and requires close daily partnership with Support as well as Product and Engineering colleagues across the United Kingdom remote setting. Responsibilities Own high-severity post-sales technical escalations from intake until resolution or complete engineering hand-off, conducting in-depth investigations and reproducing hard-to-isolate defects. Hold customer calls, extract logs and discuss evolving diagnostic theories openly. Build engineering hand-off packages requiring minimal further questions: reproducible case, log evidence with timestamps and node IDs, version matrix, impact scope, items already eliminated and proposed ownership team. Create and track confirmed bug records while preserving continuous ticket links that keep full customer context visible to engineering. Spot patterns across escalations to detect recurring or systemic issues early and convert insights into product refinements, tooling and runbooks that raise technical capability for the whole Support group. Partner with Support, customer success engineers and Product/Engineering while remaining strictly inside team boundaries. Skills & Qualifications Four or more years in technical support or escalations at a SaaS or infrastructure company with proven ownership of enterprise-level escalated accounts. Genuine problem-solver who gains energy from untangling hard ambiguous technical issues. Confidence managing live high-stakes customer calls: remaining calm, building trust and communicating clearly with frustrated or highly technical clients under pressure. Hands-on networking experience in production or laboratory settings covering TCP/IP, routing, DNS, firewalls, NAT, VPNs and load balancers. Deep familiarity with overlay networking concepts including WireGuard, UDP hole punching, STUN and comparable VPN or networking products. Code-level debugging ability: reading Go source, reasoning about goroutines, locks and channels, interpreting pprof CPU and heap…
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