engineering
Posted 2 days agoSoftware Engineer, AI Enablement
at Tailscale
CanadaRemote
Responsibilities
- 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.
- Develop infrastructure, guardrails, review practices, and documentation for the safe, secure use of AI-generated code.
- Track adoption and measure the real impact of AI tooling on engineering velocity and quality, and report back to leadership.
- Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.
Requirements
- 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.
- 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.
- 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.
- Genuine, daily, hands-on fluency with modern AI coding tools (Claude Code, Codex, Pi, or similar) — real power-user experience, not occasional use •
- 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
- experience in developer experience, platform engineering, or internal tooling •
- 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
- Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.
Experience
- 5+ years of professional software engineering experience
Benefits
- 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.
- CAN Pay Range $218,420 — $302,840 CAD
- 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!
- 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.
- 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!
- 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).
Contact
- 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 .
Additional details
- 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
- 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
- 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 evaluating or benchmarking LLMs and coding agents •
- Individual offers may vary based on experience and skill set.
- 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