Software Engineer, AI Enablement

Tailscale

Remote regions

Canada

Salary range

$160,000–$221,000/yr

Benefits

Unlimited PTO 20w maternity 16w paternity

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Responsibilities:

  • Partner with engineering leadership and co-founders to define internal AI-enablement priorities and roadmap.
  • Build and iterate on internal tools, workflows, and practices that help engineers use coding agents effectively.
  • Evaluate new AI models and tools, making clear recommendations for adoption.

Qualifications:

  • 5+ years of professional software engineering experience with hands-on fluency in modern AI coding tools.
  • Strong written and verbal communication skills for teaching and influencing engineers.
  • Comfort with ambiguity, self-directed prioritization, and product or systems thinking.

Benefits:

  • Inclusive, flexible environment with comprehensive group benefits including health, vision, and dental.
  • Unlimited paid time off and a healthy work-life integration.
  • Paid parental leave program with 20 weeks for birthing parents and 16 weeks for non-birthing parents.

Tailscale

Tailscale builds software that securely interconnects people and devices, creating an easy, sensible, and safe internet experience. Founded in 2019 and fully distributed, the company is backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

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