Software Engineer, AI Enablement

About the role

Tailscale is seeking a Software Engineer to join our AI Enablement team in a Remote (United Kingdom) position. This full-time role is central to shaping how our engineering organization uses artificial intelligence to build software more efficiently and securely. You will play a key role in influencing the adoption and effectiveness of AI across the company. The position requires a balance of technical depth and strategic thinking to turn high-level goals into actionable implementations that deliver measurable value. You will work closely with cross-functional partners to ensure AI capabilities are integrated thoughtfully into development workflows, directly impacting the productivity and tooling landscape for engineering teams globally. This role operates within the AI Enablement team and reports into the broader engineering leadership structure, ensuring alignment between AI strategy and business objectives.

What you'll do

• Collaborate with engineering leaders to define and advance our strategy for AI integration in development.
• Work on Aperture by Tailscale, our AI gateway product, and internal AI tools.
• Develop and refine the systems and practices that help engineers benefit from AI coding assistants, and assess new AI technologies for adoption.
• Identify and implement AI solutions that improve productivity for engineering and other teams.
• Establish guidelines and review processes to ensure the safe use of AI-generated code, promoting best practices without enforcing rigid tool mandates.
• Monitor the impact of AI tools on development speed and code quality, reporting findings to leadership.
• Evaluate emerging AI tools and frameworks to determine their potential value for our engineering workflows.
• Partner with product teams to design user experiences for internal AI tools and platforms.
• Analyze usage metrics and feedback to continuously improve the AI enablement stack.
• Support the rollout of new AI features through documentation, demos, and training sessions.
• Conduct proof-of-concept projects to validate new AI capabilities before broader deployment.
• Act as a subject matter expert, advising engineering teams on responsible AI usage and workflow optimization.

Requirements

• A minimum of 5 years of professional software engineering experience.
• Extensive, practical experience with AI coding assistants such as Claude Code, Codex, or Pi.
• Proven ability to build and deploy internal developer tools or automation.
• Excellent communication skills, both written and verbal, with the ability to guide engineers with varying levels of AI familiarity.
• A pragmatic approach to AI adoption, focusing on making tools easy to use and safe.
• Comfort working independently and prioritizing tasks within a developing team.
• Strong product or systems thinking to identify and prioritize impactful opportunities.
• Familiarity with version control systems and modern software development practices.
• Understanding of secure coding principles and data privacy considerations in AI implementations.
• Ability to translate complex technical concepts into actionable guidance for cross-functional stakeholders.

Nice to have

• Previous experience in developer experience, platform engineering, or internal tooling.
• Experience evaluating and benchmarking large language models and coding agents.
• Familiarity with systems programming languages like Go or Rust, in addition to Python.
• Background in security or code review practices.
• Experience in developer relations or technical advocacy.
• Background in technical project management.
• Knowledge of AI model fine-tuning and prompt engineering techniques.
• Experience with continuous integration and deployment pipelines for AI-assisted development.

Skills & tools

• AI coding tools (Claude Code, Codex, Pi, or similar)
• Python
• Go (preferred)
• Rust (preferred)

Practical notes

Salary range: £128,770 - £178,540 GBP.

Tailscale offers a competitive compensation package including base salary, equity, and comprehensive benefits.

We support remote work and offer benefits such as health, vision, and dental coverage, employer-funded retirement contributions, professional development funds, and paid parental leave.

We encourage applications from candidates who may not meet every single qualification.

All hiring decisions are made by people, though AI tools may be used in the assessment process.

Legitimate communications from Tailscale will come from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses.