Software Engineer, AI Enablement

• Help Tailscale's engineering organisation get the most out of AI-assisted development. • Join a small, high-leverage team reporting to a co-founder, working alongside the first AI enablement engineer. • Build the tools, workflows, and practices that help every engineer at Tailscale build faster and more safely with AI. • Take on a foundational role with real latitude to shape what AI enablement means at Tailscale as it scales, with direct visibility into how the whole engineering org adopts these tools. • Work remotely from anywhere in the United Kingdom at a fully distributed company.

• Have 5+ years of professional software engineering experience. • Bring genuine, daily, hands-on fluency with modern AI coding tools such as Claude Code, Codex, or Pi, as a real power user rather than an occasional one. • Have built and shipped internal tools or developer-facing automation. • Communicate strongly in writing and in person, comfortable teaching, writing, and influencing engineers at very different comfort levels with AI tooling. • Take a balanced approach to adoption, since there is no AI mandate here — the goal is making AI easy and safe so people choose it when appropriate. • Stay comfortable with ambiguity and self-directed prioritisation on a small, still-forming team. • Think in products or systems, identifying and prioritising high-leverage opportunities rather than executing a pre-set roadmap.

• Have prior experience in developer experience, platform engineering, or internal tooling. • Have evaluated or benchmarked LLMs and coding agents. • Have experience with a systems language such as Go or Rust alongside Python. • Have a background in security or code-review practices, useful for reasoning about AI and agent-generated code. • Have worked in developer relations, technical evangelism, or customer-facing developer advocacy. • Have technical project management experience.

• Partner with engineering leadership and Tailscale's technical staff to define and drive the internal AI-enablement roadmap. • Work closely with the team building Aperture by Tailscale, the AI gateway used 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. • Evaluate new models and tools, and make clear calls on what gets adopted. • Partner with engineering and non-engineering teams to find high-leverage opportunities to apply AI, measuring success by other teams shipping faster. • Establish the guardrails, review practices, and documentation that make AI-generated code safe to ship. • Act as the internal advocate who helps teams adopt good practices without mandating a single tool. • Track adoption, measure the real impact of AI tooling on velocity and quality, and report back to leadership.

• Receive a competitive total compensation package including base salary and an equity incentive plan. • Access comprehensive group benefits with no waiting period, covering health, vision, dental, and more for you and your family. • Work remote-first with support for virtual and in-person social events and a corporate co-working programme at WeWork or similar spaces. • Get employer-funded retirement contributions matched dollar-for-dollar, up to 0.75% of your eligible compensation annually. • Attend the annual company retreat and team off-sites, connecting with teammates across Canada, the US, the UK, and Singapore. • Spend $1,500 USD annually on professional development, alongside mentorship, coaching, and internal promotion opportunities. • Take flexible paid time off that supports whatever life throws your way. • Build your own home office with a company-owned laptop of your choice, monthly home internet reimbursement, and $500 USD to customise your workstation. • Take paid parental leave top-ups of 20 weeks for birthing parents and 16 weeks for non-birthing parents.

Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices wherever they are. Teams of every size, from hobbyists to multinational corporations, use Tailscale to protect their networks and share access to internal tools. The company was founded in 2019, is fully distributed, and is backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.