- Experience
- 5+ yrs
- Salary
- CAD 218,420 – CAD 302,840 / year
- Openings
- 1
- Posted
- 1 day ago
- Work mode
- Work from home
- Resume
- Required to apply
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Job description
About Tailscale
Tailscale is revolutionizing internet connectivity by creating software that enables secure and seamless connection of people and devices regardless of location. Serving users ranging from hobbyists to large global companies, Tailscale provides network protection and controlled access to internal tools. Founded in 2019 and fully distributed, the company is supported by prominent investors including Accel and CRV.
Role Overview
We are looking for a skilled and driven Software Engineer specializing in AI Enablement to join a small, impactful team dedicated to enhancing Tailscale's engineering productivity through AI-assisted development. Reporting to a co-founder and collaborating closely with the initial AI enablement engineer, you will develop tools, workflows, and approaches that empower engineers across the company to adopt AI to increase speed and safety. This foundational position offers significant influence on the AI enablement strategy as the company scales.
Primary Responsibilities
- Collaborate with engineering leaders and technical staff to craft and advance the AI enablement roadmap internally.
- Work intimately with the Aperture by Tailscale team, supporting both internal use and product integration of this AI gateway.
- Develop and refine tools, practices, and workflows that maximize engineers' benefits from AI coding agents; critically assess new AI models and tools for possible adoption.
- Identify and implement high-impact AI applications in partnership with engineering and other departments to boost development efficiency.
- Create safety protocols, review processes, and documentation to ensure AI-generated code is reliable and promote best practices without imposing mandatory solutions.
- Monitor AI tooling adoption rates, evaluate their effects on development speed and quality, and regularly report findings to leadership.
Candidate Profile
- At least five years of professional experience in software engineering.
- Extensive daily hands-on expertise with contemporary AI coding tools such as Claude Code, Codex, or Pi, showing power-user capabilities.
- Proven background in building and deploying internal tools or developer automation solutions.
- Excellent written and verbal communication skills, capable of educating and advocating across varying levels of AI familiarity among engineers.
- A balanced outlook promoting effective and secure AI use without enforcing compulsory adoption.
- Comfortable operating with ambiguity and capable of self-driven prioritization in a nascent team environment.
- Strong product and systems thinking to recognize and prioritize impactful opportunities beyond predefined plans.
Desirable Qualifications
- Experience in developer experience, platform development, or internal tooling initiatives.
- Background in assessing and benchmarking large language models and coding agents.
- Familiarity with systems programming languages like Go or Rust alongside Python.
- Knowledge of security and code review practices providing insight into AI-generated code safety.
- Experience in developer relations or technical evangelism relevant to driving internal AI adoption.
- Project management skills relevant to technical initiatives.
Compensation and Benefits
Our company emphasizes equitable pay across all levels and roles. The compensation package features a base salary, company equity, and extensive benefits, with the Canadian salary range between 218,420 CAD and 302,840 CAD annually. Benefits include health, vision, dental coverage without waiting periods, employer-matched retirement plans, a flexible and inclusive work environment with remote-first policies, professional development allowances, paid time off, parental leave top-ups, and a customizable home office budget.
Commitment to Diversity and Accessibility
We encourage applicants from historically marginalized groups to apply regardless of whether they meet every listed qualification. Our recruitment process supports accessibility accommodations and benefits from AI-assisted screening, while all hiring decisions are made by people.
Security and Authenticity Notice
Official communications during recruitment will originate only from authorized company domains to protect candidates from impersonation scams.