Tailscale seeks a Software Engineer, AI Enablement to drive AI-assisted development across the engineering organization. This role involves building tools, workflows, and practices to enhance engineer productivity and safety with AI. Requires 5+ years of software engineering experience and hands-on fluency with modern AI coding tools.
Key Highlights
Shape the future of AI enablement at Tailscale, influencing adoption across the engineering org.
Build and iterate on tools and workflows to help engineers leverage AI coding agents effectively and safely.
Partner with engineering leadership to define and drive the internal AI enablement roadmap.
Key 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.
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Technical Skills Required
Software Engineering
AI Coding Tools
Internal Tools Development
Benefits & Perks
Competitive total compensation package (base salary, equity, variable commission)
Comprehensive group benefits with no waiting period (health, vision, dental)
Remote-first company with flexible work environment and co-working program
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Nice to Have
Prior experience in developer experience, platform engineering, or internal tooling
Experience evaluating or benchmarking LLMs and coding agents
Experience with a systems language such as Go or Rust, in addition to Python
Background in security or code-review practices
Experience in developer relations, technical evangelism, or customer-facing developer advocacy
Technical project management experience
Job Description
Thank you for considering Tailscale. If this job description resonates with you, please apply. Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.
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