Software Engineer, AI Enablement

Tailscale

17h • $163,000 - $226,000 • Remote

About The Position

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.

Requirements

• 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. We don't have an 'AI mandate'; we believe that if we make AI both easy to use and safe, people will choose to use it when 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 Haves

• 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, though you don't need to be a security engineer
• Experience in developer relations, technical evangelism, or customer-facing developer advocacy — the same skills that make someone effective in external DevRel translate well to driving internal AI adoption
• Technical project management experience

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.

Benefits

• Competitive total compensation package (base salary, equity incentive plan)
• Comprehensive group benefits with no waiting period (health, vision, dental)
• Remote first company with options for co-working spaces
• Employer-funded retirement contributions (match up to 0.75% of eligible compensation)
• Support for personal and professional development ($1500 USD annually)
• Flexible, paid time off
• Home office setup (company-owned laptop, monthly internet reimbursement, $500 USD for customization)
• Paid parental leave program (20 weeks for birthing parents, 16 weeks for non-birthing parents)

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed