Jobs at Tailscale

Build Tailscale’s internal AI-enablement tools, workflows, guardrails, and practices. Partner with engineering leadership and technical teams to define the AI roadmap, evaluate coding agents and models, improve developer velocity and quality, and drive safe adoption. The role includes internal tooling, developer advocacy, documentation, impact measurement, and collaboration across engineering and non-engineering teams.

Provide Tier 1 technical support for configuration and networking issues, manage a high-volume ticket queue, meet response and resolution targets, and maintain strong customer satisfaction. Troubleshoot across multiple operating systems, explain technical concepts clearly, and collaborate with customer experience, product, and engineering teams to resolve recurring user friction and improve the product experience.