Software Engineer, AI Enablement

About Tailscale

Tailscale is transforming the Internet by creating software that enables secure connections between people and their devices regardless of location. Serving users from individual hobbyists to large enterprises, Tailscale facilitates secure network protection and internal tool sharing. Founded in 2019 and operating fully remotely, the company is supported by notable backers including Accel, CRV, Insight, Heavybit, and Uncork Capital.

Role Overview

We are looking for a motivated full-time Software Engineer specializing in AI Enablement to help maximize the impact of AI-assisted development throughout Tailscale's engineering teams. This role offers the unique opportunity to influence AI capabilities at a foundational level while working closely with senior leadership and the existing AI enablement staff to craft tools and workflows that enhance engineering efficiency and safety.

Key Responsibilities

• Collaborate with engineering leaders and technical staff to set and drive the internal AI enablement strategy.
• Contribute closely to the development of Aperture by Tailscale, an AI gateway utilized both internally and as a product offering.
• Create, update, and refine tools, workflows, and best practices that empower engineers to benefit from AI-powered coding agents, also assessing new tools and models for adoption.
• Work with engineering and other departments to identify high-impact AI application opportunities that accelerate project delivery.
• Develop and promote safe AI code generation guidelines, including establishing guardrails, code review processes, and comprehensive documentation without enforcing uniform tool mandates.
• Monitor adoption rates and measure the effectiveness of AI tools on productivity and code quality, regularly reporting insights to leadership.

Candidate Profile

• At least five years of professional experience in software engineering.
• Extensive, daily hands-on experience with modern AI coding tools such as Claude Code, Codex, or Pi, demonstrating advanced power-user proficiency.
• Proven history in developing and delivering internal utilities or automation solutions aimed at developers.
• Excellent communication skills, capable of educating and influencing teams with diverse AI proficiency levels.
• An approach focused on encouraging effective and safe AI usage rather than enforcing AI adoption.
• Comfortable navigating ambiguity and self-managing priorities within a small developing team.
• Product and system-oriented thinking to identify and seize high-value AI opportunities beyond a predefined roadmap.

Preferred Qualifications

• Experience in developer experience initiatives, platform engineering, or internal tooling.
• Skills in assessing or benchmarking large language models (LLMs) and coding agent effectiveness.
• Knowledge of systems programming languages such as Go or Rust alongside Python.
• Background in security or code review methodologies relevant to overseeing AI-generated code.
• Experience in developer relations, technical evangelism, or internal advocacy that supports AI adoption.
• Familiarity with technical project management.

Compensation and Benefits

Tailscale follows equitable compensation practices offering a comprehensive package including base salary, equity, and benefits. The UK salary range for this role is between £128,770 and £178,540 GBP. Benefits include inclusive and flexible work environments encouraging authenticity, full health, vision, and dental coverage without waiting periods, remote-first operations with optional co-working spaces, dollar-for-dollar matched retirement contributions up to a set maximum, paid company retreats and team off-sites, professional development support with an annual budget, flexible paid time off, a customizable home office setup with equipment reimbursement, and paid parental leave programs.

Diversity and Accessibility Commitment

We strive to dismantle application barriers for underrepresented groups and foster an inclusive hiring process. Accommodations are available upon request throughout recruitment. While our hiring process integrates AI tools for screening, all final hiring decisions are human-made. Beware of impersonation scams; official communications will only come from designated company domains.