Software Engineer, AI Enablement

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About Tailscale

Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

About the Role

We're seeking a talented and motivated full-time Software Engineer, AI Enablement to help Tailscale's engineering organization get the most out of AI-assisted development. You'll join a small, high-leverage team reporting to our co-founder, working alongside our first AI enablement engineer to build the tools, workflows, and practices that help every engineer at Tailscale build faster and more safely with AI. This is a foundational role — you'll have real latitude to shape what AI enablement means here as we scale, with direct visibility into how the whole engineering org adopts these tools.

Key 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.

What We Are Looking For

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

Nice to Have

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