Jobs at Tailscale

Build and maintain internal shared engineering services: improve observability, CI/CD, and infrastructure as code; operate cloud-managed services and VMs; collaborate cross-functionally, own projects end-to-end, participate in incident response, and improve system scalability and stability.

Lead resolution of high-severity post-sales technical escalations: reproduce complex bugs, perform deep-dive debugging (networking, packet analysis, pprof), run customer calls, and produce engineering-ready handoff packages. Monitor patterns, create runbooks and tooling, and partner with Support and Product/Engineering to close the loop.

Provide Tier 2 technical support for paying customers, owning escalations through resolution. Troubleshoot complex networking, VPN, SSO, and Kubernetes issues; manage ticket SLAs; mentor Tier 1; collaborate with Product and Engineering to resolve root causes and improve the user experience.