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Software Engineer, AI Enablement

Tailscale· Strategic Projects
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Hybrid (Canada)CA$218.4k - CA$302.8kfull-timePosted 2mo ago

About the role

Full-time Software Engineer focused on AI enablement to empower Tailscale's engineering organization with AI-assisted development, tooling, and safe adoption practices.

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.

Qualifications

  • 5+ years of professional software engineering experience
  • Genuine, daily, hands-on fluency with modern AI coding tools (Claude Code, Codex, Pi, or similar) — real power-user experience, not occasional use
  • Experience building and shipping internal tools or developer-facing automation
  • Strong written and verbal communication and internal advocacy skills — comfortable teaching, writing, and influencing engineers at very different comfort levels with AI tooling
  • A balanced approach — trying to get people to use AI effectively and safely where appropriate. We don't have an 'AI mandate'; we believe that if we make AI both easy to use and safe, people will choose to use it when 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, not just execute a pre-set roadmap

Skills

Required:Software engineeringAI tooling fluencyInternal tooling / automationCommunication / advocacy

Benefits

  • An inclusive, flexible environment where you can be your authentic self
  • A competitive total compensation package including base salary, equity, and variable compensation
  • Comprehensive group benefits with no waiting period
  • Remote first company with optional in-person collaboration as needed
  • Employer-funded retirement contributions matched up to 0.75% of eligible compensation
  • Annual company retreat and team off-sites in multiple locations
  • $1500 USD annually for professional development
  • Paid time off and flexible PTO program
  • Build-your-own home office setup including company laptop choice, home internet reimbursement, and $500 USD for workstation customization
  • Paid parental leave program (20 weeks for birthing parents, 16 weeks for non-birthing parents)
Last updated Oct 15, 2026. Interested? Apply on the company site.

About Tailscale

Secure Connectivity for AI, IoT & Multi-Cloud

The connectivity platform for devs, IT, and security teams. Zero Trust identity-based access that deploys in minutes and scales to every resource.

SecurityNetworkingZero TrustIdentity-based accessMulti-Cloud
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