Jobs at Tailscale

Serve as Tier 2 escalation for technically complex SaaS support tickets. Troubleshoot networking/VPN issues, ACLs, subnet routing, SSO integrations, and Kubernetes basics. Maintain SLAs, high CSAT, mentor Tier 1, collaborate with Product/Eng to remove recurring friction, and contribute documentation and improvements.

Build demos, sample apps, docs, tools, and technical content to improve developer experience for Tailscale products; engage with developer communities, represent the company at events, contribute to open source, and work cross-functionally to reduce developer friction and shape product experience.

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.