Ever feel like modern software development moves at a dizzying pace? At Tailscale, we think building secure networks should feel effortless, and we want our internal engineering workflow to match that exact philosophy. We are looking for a Software Engineer for AI Enablement to join our fully remote, worldwide team. You will partner directly with our co-founder and our first AI enablement engineer on a tight-knit squad dedicated to supercharging how our developers use artificial intelligence. If you love tinkering with cutting edge tooling and want to shape how a top tier engineering organization codes with AI, this is your chance to jump in.

Overview

Tailscale is on a mission to make secure connections simple for everyone from independent hobbyists to massive global enterprises. Founded in 2019 as a fully distributed company and backed by top tier investors, we are reimagining networking for the modern internet. In this role, you will build internal systems, evaluate emerging AI models and coding assistants, and create workflows that genuinely save our engineers time and mental energy every single day.

Key Responsibilities

Design and build internal tools that integrate AI assistance seamlessly into our daily engineering routines.
Evaluate new machine learning models, coding copilots, and automation frameworks to see what actually works.
Collaborate closely with engineers across the company to understand bottlenecks and create tailored AI solutions.
Establish best practices for secure and effective AI-assisted software development.
Measure the impact of our enablement initiatives and iterate rapidly based on team feedback.

Requirements

Strong software engineering background with professional experience building and shipping applications.
Deep curiosity about artificial intelligence, large language models, and developer tooling.
Comfort working autonomously in a fully remote environment distributed across multiple time zones.
A collaborative mindset and a passion for helping other engineers succeed.
Ability to write clean, maintainable code and quickly adapt to new technologies.

What You'll Gain

You will join a small, high leverage team where your voice truly matters and your work directly impacts every engineer at the company. We offer a flexible, asynchronous remote culture that trusts you to manage your time and do your best work. Plus, you will get to work alongside founders and builders who care deeply about developer experience, internet security, and making software fun again.