Software Engineer, AI Enablement
New
T
TailscaleSoftware Engineering
Remote (Canada)Full-TimeMiddle
Salary$218,420 — $302,840 CAD
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Job Details
- Experience
- 5+ years
- Required Skills
- PythonGoRust
Requirements
- 5+ years of professional software engineering experience.
- Genuine, daily, hands-on fluency with modern AI coding tools (e.g., Claude Code, Codex, Pi).
- Proven experience building and shipping internal tools or developer-facing automation.
- Strong written and verbal communication skills with experience in internal advocacy, teaching, or influencing.
- Ability to balance AI safety with practical adoption and ease of use.
- Comfort with ambiguity and self-directed prioritization.
- Product or systems thinking mindset to identify high-leverage opportunities.
- Preferred: Experience in developer experience, platform engineering, or internal tooling.
- Preferred: Experience evaluating or benchmarking LLMs and coding agents.
- Preferred: Proficiency in systems languages such as Go, Rust, or Python.
- Preferred: Background in security, code-review practices, technical evangelism, or developer relations.
Responsibilities
- Partner with engineering leadership and technical staff to define internal AI-enablement priorities and the roadmap.
- Contribute to the development of Aperture by Tailscale, an AI gateway used internally and provided as a product.
- Build, maintain, and iterate on internal tools, workflows, and best practices for using coding agents like Claude Code, Codex, and others.
- Evaluate new AI models, agents, and tools to make recommendations for adoption.
- Collaborate across engineering and non-engineering teams to apply AI to day-to-day workflows.
- Develop infrastructure, guardrails, review practices, and documentation for the safe use of AI-generated code.
- Advocate for effective AI practices through documentation, internal talks, and hands-on coaching.
- Track adoption and measure the impact of AI tooling on engineering velocity and quality.
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