218K–303K CAD / year
Software Engineer, AI Enablement
AIRemote — unknown
Published on 2026-10-08
These details were extracted automatically from the original listing. They may not be complete or fully up to date — it's worth checking the original job post.
About this role
Tailscale is seeking a Software Engineer for AI Enablement to enhance AI-assisted development within their engineering organization. This role involves building tools, workflows, and practices to help engineers leverage AI effectively and safely. The position reports to a co-founder and is key in shaping AI strategies as the company scales.
About the company
Tailscale builds a zero-config mesh VPN on WireGuard so teams can securely connect devices, servers, and cloud resources without traditional VPN complexity.
What you'll do
- Define and drive the internal AI-enablement roadmap
- Work closely with the team building Aperture by Tailscale
- Build and iterate on AI development tools and workflows
- Identify opportunities to apply AI across teams
- Establish safety practices for AI-generated code
- Measure the impact of AI tooling on development
What we're looking for
- 5+ years of software engineering experience
- Hands-on fluency with AI coding tools
- Experience building internal tools or automation
- Strong communication and advocacy skills
- Balanced approach to AI adoption
- Comfort with ambiguity on a forming team
Nice to have
- Experience in developer experience or internal tooling
- Experience evaluating coding agents
- Familiarity with systems language like Go or Rust
- Background in security or code review
- Experience in developer relations or advocacy
Benefits
- Flexible working environment
- Comprehensive group benefits
- Employer-funded retirement contributions
- Annual professional development stipend
- Paid parental leave program