Software Engineer, AI Enablement

Description: Seeking a full-time Software Engineer, AI Enablement to enhance AI-assisted development at Tailscale. Join a small team to build tools and workflows that help engineers utilize AI effectively and safely. Requirements: 5+ years of professional software engineering experience. Hands-on fluency with modern AI coding tools (e.g., Claude Code, Codex). Experience in building internal tools or developer-facing automation. Strong communication and advocacy skills for teaching AI tooling. Ability to prioritize and navigate ambiguity in a small team. Product or systems thinking to identify high-leverage opportunities. Benefits: Inclusive and flexible work environment. Competitive total compensation package including salary and equity. Comprehensive group benefits with no waiting period. Remote-first company with options for in-office collaboration. Employer-funded retirement contributions. Annual budget for professional development ($1500 USD). Flexible paid time off program. Build-your-own home office setup with reimbursement options. Paid parental leave program.