Tailscale
Software Engineer, AI Enablement
Remote (Canada) +3 · Remote · Full-time · Posted Jul 24, 2026
- Location
- Remote (Canada)
Canada
United Kingdom
United States - Experience
- 5+ years of professional software engineering experience.
About the job
Build tools, workflows, and practices that help Tailscale’s engineering organization use AI-assisted development effectively and safely.
What you'll do
- Define and drive the internal AI-enablement roadmap with engineering leadership and technical staff.
- Build and improve tools and workflows for coding agents; evaluate models and tools for adoption.
- Establish safe-use guardrails and review practices, support AI adoption across teams, and measure impact on velocity and quality.
What they ask for
- 5+ years of professional software engineering experience.
- Daily, hands-on fluency with modern AI coding tools such as Claude Code, Codex, Pi, or similar.
- Experience building and shipping internal tools or developer-facing automation.
- Strong written and verbal communication and internal advocacy skills.
Nice to have
- Experience in developer experience, platform engineering, or internal tooling.
- Experience evaluating or benchmarking LLMs and coding agents; Go or Rust experience; security or code-review background; developer advocacy; or technical project management.
Pay
$218,420 — $302,840 CAD (base salary)
Tools
Claude Code, Codex, Pi, Go, Rust, Python
AI focus
Enable safe and effective AI-assisted development by building coding-agent tools and workflows, evaluating models, setting guardrails, and measuring adoption and impact.
Model-written summary · the original posting is authoritative