Software Engineer, AI Enablement

Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices. They are seeking a full-time Software Engineer, AI Enablement to help the engineering organization leverage AI-assisted development, focusing on building tools and practices that enhance coding efficiency and safety.

Responsibilities:

• Partner with engineering leadership and Tailscale's technical staff to define and drive our internal AI-enablement roadmap
• Work closely with the team building Aperture by Tailscale, our AI gateway used both internally and offered as a product
• Build and iterate on the tools, workflows, and shared practices that help engineers get real value from coding agents — and evaluate new models and tools, making clear calls on what we adopt
• Partner with engineering and non-engineering teams to find high-leverage opportunities to apply AI — this is a support function, so success means other teams shipping faster because of what you've built
• Establish the guardrails, review practices, and documentation that make AI-generated code safe to ship, and act as the internal advocate who helps teams adopt good practices without mandating a single tool
• Track adoption and measure the real impact of AI tooling on velocity and quality, and report back to leadership

Requirements:

• 5+ years of professional software engineering experience
• Genuine, daily, hands-on fluency with modern AI coding tools (Claude Code, Codex, Pi, or similar) — real power-user experience, not occasional use
• Experience building and shipping internal tools or developer-facing automation
• Strong written and verbal communication and internal advocacy skills — comfortable teaching, writing, and influencing engineers at very different comfort levels with AI tooling
• A balanced approach — trying to get people to use AI effectively and safely where appropriate. We don't have an 'AI mandate'; we believe that if we make AI both easy to use and safe, people will choose to use it when appropriate
• Comfort with ambiguity and self-directed prioritization on a small, still-forming team
• Product or systems thinking — able to identify and prioritize high-leverage opportunities, not just execute a pre-set roadmap
• Prior experience in developer experience, platform engineering, or internal tooling
• Experience evaluating or benchmarking LLMs and coding agents
• Experience with a systems language such as Go or Rust, in addition to Python
• Background in security or code-review practices — helpful for reasoning about AI/agent-generated code, though you don't need to be a security engineer
• Experience in developer relations, technical evangelism, or customer-facing developer advocacy — the same skills that make someone effective in external DevRel translate well to driving internal AI adoption
• Technical project management experience