Jobs at Tailscale

Build internal AI enablement tools, workflows, and guardrails to help engineers use coding agents safely and productively. Evaluate models and agents, partner with teams to apply AI, track adoption and impact, and provide documentation, training, and advocacy across the engineering organization.

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.