Tailscale
Software Engineer, Strategic Projects
Remote (Canada) +2 · Remote · Full-time · Posted Aug 5, 2026
- Location
- Remote (Canada)
Canada
United States - Experience
- No specific number of years stated; experience taking software from prototype to production in startup-like environments is sought.
About the job
Takes experimental connectivity and AI-related prototypes from early design through production, ensuring they are secure, reliable, maintainable, and ready for customers.
What you'll do
- Shape prototypes with product-minded engineers and help design their path to production.
- Harden prototypes with testing, observability, error handling, operational tooling, and security and review practices.
- Integrate Tailscale with reference customers and close reliability, edge-case, and supportability gaps.
What they ask for
- Go experience; comfort integrating third-party APIs and basic networking.
- Heavy daily use of coding agents and LLMs in engineering, with a perspective on their strengths, limitations, and production safeguards.
- Experience hardening, stabilizing, and maintaining production software.
- Comfort working independently in a remote, fast-paced environment with shifting priorities and technical customers.
Nice to have
- Production service operations experience, including observability, on-call, incident response, performance, or reliability work.
- Identity infrastructure or authentication experience; LLM application development; Tailscale/networking familiarity; open-source participation; or Python, Rust, and/or TypeScript.
Pay
$218,420 — $302,840 CAD (base salary)
Tools
Go, Claude Code, Cursor, LLMs, OAuth, OIDC, SAML, SCIM
AI focus
Uses coding agents and LLMs heavily in engineering; establishes review, testing, and security practices for agent-generated code. The team also develops AI-related connectivity initiatives, including an identity-aware LLM gateway.
Model-written summary · the original posting is authoritative