AI Enablement Engineer: Build Internal Dev Tools (Remote)

Tailscale; United States; Remote; CAD 218,000 - 303,000; Full time

Benefits offered by this job

Remote first environment

Competitive compensation

Equity and benefits package

Professional development allowance

Paid time off

Build-your-own home office setup with$

Job summary

Tailscale is seeking a talented Software Engineer, AI Enablement, to help unlock AI-assisted development across our engineering org. You’ll shape the tools, workflows, and practices that let engineers build faster and safer with AI, reporting to the co-founder on a foundational, high-leverage team.

You’ll partner with leadership to define the roadmap, work on Aperture by Tailscale, and define guardrails for AI-generated code while measuring adoption and outcomes across the company.

Qualifications

• 5+ years of professional software engineering experience.
• Fluency with modern AI coding tools (Claude Code, Codex, Pi or similar).
• Experience building internal tools or developer-facing automation.
• Strong written and verbal communication and advocacy skills.
• Balance AI adoption with safety and governance.

Responsibilities

• Define and drive our internal AI-enablement roadmap with engineering leadership.
• Collaborate on Aperture by Tailscale, our AI gateway used internally and as a product.
• Build tools, workflows and practices that help engineers leverage AI for faster, safer coding.
• Identify high-leverage opportunities to apply AI across teams and measure impact.
• Establish guardrails, review practices and docs for safe, ship-ready AI-generated code.
• Track adoption, report velocity and quality improvements to leadership.

Skills

5+ years experience

AI tool fluency

Internal tools development

Communication skills

Product or systems thinking

Ambiguity tolerance

Tools

Claude Code

Codex

Pi

Job description

Tailscale is seeking a talented Software Engineer, AI Enablement, to help unlock AI-assisted development across our engineering org. You’ll shape the tools, workflows, and practices that let engineers build faster and safer with AI, reporting to the co-founder on a foundational, high-leverage team.

You’ll partner with leadership to define the roadmap, work on Aperture by Tailscale, and define guardrails for AI-generated code while measuring adoption and outcomes across the company.