Teams at Tailscale

Provide high-touch executive support to the VP of Engineering: manage complex calendars, meetings, travel, and communications; coordinate cross-functional initiatives and projects; prepare briefings and presentations; track decisions and action items; improve operational processes and systems; partner with CTO Chief of Staff and other leaders to drive organizational effectiveness in a distributed, fast-moving engineering organization.

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.

Lead resolution of high-severity post-sales escalations: investigate and reproduce complex networking and software issues, run customer calls, collect logs and evidence, create engineering-ready handoff packages, identify systemic patterns, and improve tooling and runbooks to raise Support's technical capability.