Software Engineer, Tailscale

• 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
• Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic!

Desirable

• 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
• 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