Skip to content
ITA Jobs
All vacancies
Tailscale logo

Software Engineer, AI Enablement

Tailscale

Remote · CanadaSalary not disclosedfull-timeTailscale Careers

We're seeking a talented and motivated full-time Software Engineer, AI Enablement to help Tailscale's engineering organization get the most out of AI-assisted development. You'll join a small, high-leverage team reporting to our co-founder, working alongside our first AI enablement engineer to build the tools, workflows, and practices that help every engineer at Tailscale build faster and more safely with AI.

Responsibilities

  • Partner with engineering leadership and Tailscale's technical staff to define and drive our internal AI-enablement roadmap.
  • Work closely with the team building Aperture by Tailscale, our AI gateway used both internally and offered as a product.
  • Build and iterate on the tools, workflows, and shared practices that help engineers get real value from coding agents — and evaluate new models and tools, making clear calls on what we adopt.
  • Partner with engineering and non-engineering teams to find high-leverage opportunities to apply AI — this is a support function, so success means other teams shipping faster because of what you've built.
  • Establish the guardrails, review practices, and documentation that make AI-generated code safe to ship, and act as the internal advocate who helps teams adopt good practices without mandating a single tool.
  • Track adoption and measure the real impact of AI tooling on velocity and quality, and report back to leadership.

Languages

    Work format
    Remote
    Seniority
    Mid
    Posted
    24 Jul 2026
    Last verified
    In the last 5 days

    Similar roles

    Keep looking