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Software Engineer, AI Enablement

2 months, 2 weeks ago
Canada
Full-time
Senior
Software Engineer
Software Development
Go LLM Python Rust
Apply Now
Tailscale

Tailscale

Tailscale is a zero config VPN service that simplifies network security and connectivity for teams of any scale, offering easy deployment, minimal latency, and compatibility with existing services.

Diversified Telecommunication Services
51-250
Founded 2019
$115M raised
View All Jobs 11

Description

  • Partner with engineering leadership and technical staff to define internal AI enablement priorities and roadmap.
  • Work with the team building Aperture by Tailscale, the company’s AI gateway product.
  • Build and maintain internal tools, workflows, and practices that help engineers use AI coding tools more effectively.
  • Evaluate new AI models, agents, and tools and recommend what to adopt.
  • Identify high-leverage ways AI can improve day-to-day work across engineering and non-engineering teams.
  • Develop infrastructure, guardrails, review practices, and documentation for 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.
  • Balance hands-on building, teaching, and prioritization in a small, high-leverage team.

Requirements

  • 5+ years of professional software engineering experience.
  • Daily, hands-on fluency with modern AI coding tools such as Claude Code, Codex, Pi, or similar.
  • Experience building and shipping internal tools or developer-facing automation.
  • Strong written and verbal communication skills for teaching and internal advocacy.
  • Ability to guide teams toward safe and effective AI use without mandating a single workflow.
  • Comfort with ambiguity and self-directed prioritization on a small, evolving team.
  • Product or systems thinking with an ability to prioritize high-leverage opportunities.
  • Experience in developer experience, platform engineering, or internal tooling (preferred).
  • Experience evaluating or benchmarking LLMs and coding agents (preferred).
  • Experience with a systems language such as Go or Rust, in addition to Python (preferred).
  • Background in security or code-review practices for AI-generated code (preferred).
  • Experience in developer relations, technical evangelism, or developer advocacy (preferred).
  • Technical project management experience (preferred).

Benefits

  • Competitive total compensation including base salary, equity, and variable commission for quota-based roles.
  • CAN base salary range of $218,420 to $302,840 CAD.
  • Comprehensive health, vision, and dental benefits with no waiting period.
  • Remote-first, flexible work environment.
  • Employer-funded retirement contributions with dollar-for-dollar matching up to 0.75% of eligible compensation.
  • $1,500 USD annually for professional development, plus mentorship, coaching, and internal promotion opportunities.
  • Flexible paid time off.
  • Home office support including a company-owned laptop, monthly internet reimbursement, and $500 USD for workstation setup.
  • Paid parental leave top-ups: 20 weeks for birthing parents and 16 weeks for non-birthing parents.
  • Annual company retreat and team off-sites with in-person collaboration opportunities.

Interested in this position?

Apply directly on the company website

Apply Now

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