Teams at Tailscale

Develop and maintain Tailscale's Windows client and contribute to cross-platform client and backend code. Build UI and platform integrations using WinUI/Windows native frameworks, write unit and integration tests, implement Windows platform features while preserving compatibility, and collaborate asynchronously across a distributed engineering team.

Provide Tier 2 technical support and escalations for Tailscale customers: troubleshoot complex networking and SSO issues, manage ticket SLAs, mentor Tier 1, collaborate with Product/Eng, and contribute to documentation and recurring friction elimination.

Work with product-minded engineers to turn AI-native prototypes (LLM gateways, agentic systems, proxies) into production-grade services: hardening, observability, security reviews, integrations with reference customers, and operational tooling to ensure reliability and maintainability.