Tailscale jobs

Tailscale is hiring a Software Engineering Manager for its Strategic Projects team, reporting to the co-founder and Chief Strategy Officer, to lead a small group of senior engineers building AI-native initiatives like Aperture (an identity-aware LLM gateway) that showcase Tailscale's connectivity infrastructure for both internal use and customer-facing products. Key responsibilities include managing and mentoring engineers, driving adoption of platform primitives, owning the quality bar for externally-visible artifacts (reference architectures, open source, customer integrations), establishing best practices for coding agents and LLMs, hiring and developing talent, and collaborating cross-functionally on fast-moving prototypes that often graduate to production. You'll need substantial experience managing engineering teams, proficiency in Go, heavy hands-on daily use of coding agents like Claude Code or Cursor with a clear point of view on their security and review practices, comfort with exploratory customer-facing engineering, and adaptability to a strategy-team cadence with shifting priorities and tight timelines. This is a fully remote role requiring ~10-15% travel (primarily North America with potential EU/APAC trips), with a competitive package including CAD $276,040–$344,380 base salary plus equity and comprehensive benefits. A standout requirement: deep, daily expertise with AI coding agents and the ability to coach senior engineers in leveraging them effectively while maintaining production standards—this is central to how the team operates.

Tailscale is seeking a Team Lead, Customer Support to establish APAC operations from Singapore, managing 8-10 support engineers and overseeing SLA/SLO compliance, hiring, and technical escalations. The role requires 6+ years in technical SaaS support, 2+ years in leadership, and networking fundamentals expertise. This is a fully remote but Singapore-based position reporting to VP of Customer Engineering.