[Hiring] Software Engineer, AI Enablement @Tailscale

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 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.

Qualifications

• 5+ years of professional software engineering experience.
• Genuine, daily, hands-on fluency with modern AI coding tools (Claude Code, Codex, Pi, or similar) — real power-user experience, not occasional use.
• Experience building and shipping internal tools or developer-facing automation.
• Strong written and verbal communication and internal advocacy skills — comfortable teaching, writing, and influencing engineers at very different comfort levels with AI tooling.
• A balanced approach — trying to get people to use AI effectively and safely where appropriate.
• 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, not just execute a pre-set roadmap.

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 — helpful for reasoning about AI/agent-generated code.
• 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 incentive plan, and variable commission (for quota-based roles).
• Comprehensive group benefits with no waiting period, covering health, vision, dental, and more for you and your family!
• Remote first company — most of our teams work fully remotely.
• Employer-funded retirement contributions, matching your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.
• Connect with other Tailscalars IRL through annual company retreats and team off-sites.
• Support for your personal and professional development with $1500 USD annually for professional development.
• Flexible, paid time off program supporting you for any situation life throws your way.
• A build-your-own home office setup with a company-owned laptop and $500 USD to customize your workstation.
• Paid parental leave program with top-ups for birthing and non-birthing parents.