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Salary: USD 163,000 - 0 / annual
Tailscale is seeking a Software Engineer, AI Enablement to help the engineering organization adopt and scale AI-assisted development practices. You'll join a small, high-leverage team reporting to a co-founder, working alongside the first AI enablement engineer to build tools, workflows, and practices that enable every engineer 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 through documentation, talks, and coaching; tracking adoption metrics and impact on engineering velocity; and balancing hands-on building, internal teaching, and prioritization.
You'll need 5+ years of professional software engineering experience with genuine, daily fluency in modern AI coding tools (not occasional use). Strong experience building and shipping internal tools or developer-facing automation is essential. Excellent written and verbal communication skills are critical—you'll be teaching and influencing engineers at very different comfort levels with AI. You should have a balanced, pragmatic approach to AI adoption: making tools easy to use and safe, letting engineers choose when to use them rather than mandating adoption. Comfort with ambiguity and self-directed prioritization on a small, forming team is important. Product or systems thinking—identifying and prioritizing high-leverage opportunities—is valued.
Nice-to-have skills include prior experience in developer experience, platform engineering, or internal tooling; experience evaluating or benchmarking LLMs and coding agents; systems language experience (Go, Rust) in addition to Python; background in security or code-review practices; 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.
