Software Engineer, AI Enablement

Role Description

We're seeking a talented and motivated full-time Software Engineer, AI Enablement to help Tailscale's engineering organization get the most out of AI-assisted development. You'll join a small, high-leverage team reporting to our co-founder, working alongside our first AI enablement engineer to build the tools, workflows, and practices that help every engineer at Tailscale build faster and more safely with AI. This is a foundational role — you'll have real latitude to shape what AI enablement means here as we scale, with direct visibility into how the whole engineering org adopts these tools.

Key Responsibilities

• Partner with engineering leadership, our co-founder and members of technical staff to define Tailscale's internal AI-enablement priorities and roadmap.
• Work with the team that’s building Aperture by Tailscale – our AI gateway that we both use internally and provide as a product.
• Build, maintain, and iterate on internal tools, workflows, and shareable practices (skills, development environments, internal tooling) that help engineers use coding agents like Claude Code, Codex, OpenCode, and Pi more effectively.
• Evaluate new AI models, agents, and tools, and make clear recommendations on what to adopt and why.
• Work directly with both engineering and non-engineering teams across the company to find high-leverage opportunities to apply AI to their day-to-day work.
• Develop infrastructure, guardrails, review practices, and documentation for the safe, secure use of AI-generated code.
• Act as an internal advocate for effective AI practices — through documentation, internal talks, and hands-on coaching.
• Track adoption and measure the real impact of AI tooling on engineering velocity and quality, and report back to leadership.
• Expect the day-to-day to span hands-on building, internal teaching/evangelism, and prioritization.

Qualifications

• 5+ years of professional software engineering experience.
• Genuine, daily, hands-on fluency with modern AI coding tools (Claude Code, Codex, Pi, or similar).
• Experience building and shipping internal tools or developer-facing automation.
• Strong written and verbal communication and internal advocacy skills.
• A balanced approach to using AI effectively and safely.
• Comfort with ambiguity and self-directed prioritization on a small, still-forming team.
• Product or systems thinking — able to identify and prioritize high-leverage opportunities.

Requirements

• 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.

Benefits

• An inclusive, flexible environment where you can be your authentic self.
• A competitive total compensation package including base salary, equity, and variable commission.
• Comprehensive group benefits with no waiting period.
• Remote first company with flexibility in how and when you work.
• Employer-funded retirement contributions with matching.
• Connect with other Tailscalars IRL through annual retreats and team off-sites.
• Support for personal and professional development with $1500 USD annually for professional development.
• Paid time off and a flexible program supporting work-life integration.
• A build-your-own home office setup with a company-owned laptop and reimbursement for home internet.
• Paid parental leave program with top-ups for new parents.