Tailscale
Software Engineer, AI Enablement
- Confirmed live in the last 24 hours
- $163k–$226k
- Mid level
- Full-time
- Remote (United States)
- 5+ yrs exp
- Added 2 months ago
About this role
Tailscale seeks a Software Engineer, AI Enablement to build tools and practices that help their engineering organization leverage AI for faster and safer development. You'll collaborate with engineering teams to define and drive an internal AI roadmap, focusing on adoption, safety, and impact measurement. This is a foundational role with significant opportunity to shape the company’s AI strategy.
What you'll do
- Define and drive the internal AI enablement roadmap.
- Build and iterate on tools and workflows for AI-assisted coding.
- Partner with engineering teams to identify high-impact AI applications.
- Establish guidelines and review practices for AI-generated code safety.
- Track AI tooling adoption and measure its impact on engineering velocity and quality.
- Collaborate with the team building Tailscale's AI gateway, Aperture.
What they're looking for
- AI coding tools (Claude Code, Codex, Pi)
- Internal tooling development
- Developer experience
- Written and verbal communication
- Internal advocacy
- Product thinking
- Systems thinking
- Python
Benefits
- Remote-first work environment
- Competitive total compensation package (base salary, equity, and commission)
- Comprehensive group benefits (health, vision, dental)
- Employer-funded retirement contributions
- Personal and professional development support ($1500 USD)
- Opportunities for in-person connection and team collaboration
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Tailscale
Likely interview questions
- Describe your experience using modern AI coding tools like Claude Code or Codex. Can you share a specific example of how you've used these tools to improve your development workflow?
- How would you approach defining and prioritizing an AI enablement roadmap for a software engineering organization?