New

Software Engineer, AI Enablement

Remote (Canada)

About Tailscale 

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.

Job 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 — this is a support/enablement function, not a standalone product team, so success means other teams shipping faster because of what you've built.
  • 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 — meeting teams where they are rather than mandating a single tool or workflow.
  • 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 — on a team this size, you'll move between all three regularly.

What We Are Looking For

  • 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

As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale's compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire's base salary. Individual offers may vary based on experience and skill set.

CAN Pay Range

$218,420 - $302,840 CAD

Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic!

What We Offer

  • An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.
  • A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).
  • Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family!
  • Remote first company—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.
  • Employer-funded retirement contributions. Tailscale will match 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. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.
  • Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities. 
  • Paid time off and a healthy work-life integration. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world! 
  • A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own. 
  • Paid parental leave program. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).

Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.

Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.

Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.

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