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Software Engineer, AI Enablement

Tailscale· Strategic Projects
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Remote$163k - $226kfull-timePosted 2mo ago

About the role

Full-time software engineer focusing on AI enablement to build tools, workflows, and practices that help Tailscale engineers leverage AI safely and effectively. Remote (United States). Reports to co-founder and works with the first AI enablement engineer to shape AI enablement program across the engineering organization.

Responsibilities

  • Partner with engineering leadership and technical staff to define and drive the 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 tools, workflows, and shared practices that help engineers get real value from coding agents — 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 guardrails, review practices, and documentation that make AI-generated code safe to ship, and advocate for 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
  • 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 different comfort levels with AI tooling
  • Balanced approach to using AI safely and effectively; no AI mandate; focus on making AI easy to use and safe
  • Comfort with ambiguity and self-directed prioritization on a small, forming team
  • Product or systems thinking — identify and prioritize high-leverage opportunities beyond a pre-set roadmap

Skills

Required:Software engineeringAI tooling fluencyInternal tooling / automationCommunication / advocacySystem thinking

Benefits

  • An inclusive, flexible environment
  • Competitive total compensation package (base + equity + variable compensation)
  • Comprehensive group benefits (health, vision, dental)
  • Remote first company with optional in-office collaboration as needed
  • Employer-funded retirement contributions (matching up to 0.75% of eligible compensation)
  • Annual company retreat and distributed collaboration opportunities
  • $1500 USD annually for professional development
  • Paid time off with flexible PTO
  • Build-your-own home office setup (laptop choice, internet reimbursement, workstation stipend)
  • Paid parental leave (20 weeks birthing parents, 16 weeks non-birthing)
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
Company profileWebsite

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