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Salary: CAD 218,420 - 0 / annual
Tailscale is seeking a Software Engineer, AI Enablement to help the engineering organization maximize the value of AI-assisted development tools. This is a foundational role on a small, high-leverage team reporting directly to a co-founder, working alongside the first AI enablement engineer to build tools, workflows, and practices that enable every engineer at Tailscale to build faster and more safely with AI.
Key responsibilities include partnering with engineering leadership to define AI-enablement priorities and roadmap; working with the team building Aperture (Tailscale's internal AI gateway and product); building and iterating on internal tools, workflows, and practices that help engineers use coding agents like Claude Code, Codex, and OpenCode more effectively; evaluating new AI models and tools with clear recommendations; identifying high-leverage opportunities to apply AI across engineering and non-engineering teams; developing infrastructure, guardrails, and documentation for safe AI-generated code use; acting as an internal advocate for effective AI practices through documentation, talks, and coaching; tracking adoption metrics and impact on engineering velocity; and balancing hands-on building, internal teaching, and prioritization.
Required qualifications: 5+ years of professional software engineering experience; genuine, daily hands-on fluency with modern AI coding tools (power-user level, not occasional use); experience building and shipping internal tools or developer-facing automation; strong written and verbal communication and internal advocacy skills; balanced approach to AI adoption (safety and ease of use); comfort with ambiguity and self-directed prioritization on a forming team; and product or systems thinking to identify high-leverage opportunities.
Nice-to-have skills include developer experience or platform engineering background, LLM/coding agent evaluation experience, systems language proficiency (Go, Rust), security or code-review background, developer relations or technical evangelism experience, and technical project management experience.
About Tailscale
AI / Data / Infrastructure; SaaS / Enterprise Software — secure networking platform built on WireGuard.
