Software Engineer, AI Enablement

Overview

Job Description

Responsibilities

• - Partner with engineering leadership, our co-founder and members of technical staff to define Tailscale's internal AI-enablement priorities and roadmap.
• - Work with the team that’s building Aperture by Tailscale – our AI gateway that we both use internally and provide as a product.
• - Build, maintain, and iterate on internal tools, workflows, and shareable practices (skills, development environments, internal tooling) that help engineers use coding agents like Claude Code, Codex, OpenCode, and Pi more effectively.
• - Evaluate new AI models, agents, and tools, and make clear recommendations on what to adopt and why.
• - Work directly with both engineering and non-engineering teams across the company to find high-leverage opportunities to apply AI to their day-to-day work.
• - Develop infrastructure, guardrails, review practices, and documentation for the safe, secure use of AI-generated code.
• - Act as an internal advocate for effective AI practices — through documentation, internal talks, and hands-on coaching.
• - Track adoption and measure the real impact of AI tooling on engineering velocity and quality, and report back to leadership.

Required Skills

• - 5+ years of professional software engineering experience
• - Genuine, daily, hands-on fluency with modern AI coding tools (Claude Code, Codex, Pi, or similar)
• - Experience building and shipping internal tools or developer-facing automation
• - Strong written and verbal communication and internal advocacy skills
• - A balanced approach — trying to get people to use AI effectively and safely where 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.

Benefits

• - An inclusive, flexible environment where you can be your authentic self.
• - A competitive total compensation package.
• - Comprehensive group benefits with no waiting period.
• - Remote first company — most of our teams work fully remotely.
• - Employer-funded retirement contributions.
• - Support for your personal and professional development.
• - Paid time off and a healthy work-life integration.
• - A build-your-own home office setup.
• - Paid parental leave program.