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Tailscale

Simple, secure networks for teams of any scale. Built on WireGuard.

Software Engineer, AI Enablement

AI EngineerMachine Learning EngineerFull TimeRemoteSeniorTeam 51-200Since 2020H1B No SponsorCompany SiteLinkedIn

Location

Canada

Posted

6 days ago

Salary

$218.4K - $302.8K / year

Seniority

Senior

Bachelor Degree5 yrs expEnglish

Job Description

Software Engineer, AI Enablement

Tailscale

• Partner with engineering leadership to define Tailscale's internal AI-enablement priorities and roadmap. • Work with the team that’s building Aperture by Tailscale – our AI gateway. • Build, maintain, and iterate on internal tools and workflows. • Evaluate new AI models, agents, and tools. • Work directly with both engineering and non-engineering teams to find opportunities to apply AI. • Develop infrastructure, guardrails, review practices, and documentation for the safe use of AI-generated code. • Act as an internal advocate for effective AI practices. • Track adoption and measure the real impact of AI tooling on engineering velocity and quality. • Expect the day-to-day to span hands-on building, teaching, and prioritization.

Job Requirements

  • 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.
  • Connect with other Tailscalars IRL.
  • 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.

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