Software Engineer, AI Enablement

Tailscale is building the new Internet 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.

About the role

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.

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.

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 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, 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

Pay

US Pay Range $163,000—$226,000 USD

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 with virtual and in-person social events, and a corporate co-working program (e.g., WeWork).
• Employer-funded retirement contributions with dollar-for-dollar matching up to 0.75% of eligible compensation.
• Annual company retreat, team off-sites, and opportunities for in-person collaboration across Canada, the United States, the United Kingdom, and Singapore.
• $1500 USD annually for professional development, mentorship, coaching, and internal promotion opportunities.
• Flexible, paid time off program supporting work-life integration.
• Build-your-own home office setup with a company-owned laptop (Mac or PC), monthly home internet reimbursement, and $500 USD to customize your workstation.
• Paid parental leave program with 20 weeks for birthing parents and 16 weeks for non-birthing parents.