Software Engineer, AI Enablement

Tailscale is seeking a Software Engineer, AI Enablement to help its engineering organization use AI-assisted development effectively and safely. The role will build tools, workflows, and practices, guide adoption, and measure the impact of AI tooling across teams.

Responsibilities

• Partner with engineering leadership and Tailscale's technical staff to define and drive our internal AI-enablement roadmap
• Work closely with the team building Aperture by Tailscale, our AI gateway used both internally and offered as a product
• Build and iterate on the tools, workflows, and shared practices that help engineers get real value from coding agents — and evaluate new models and tools, making clear calls on what we adopt
• Partner with engineering and non-engineering teams to find high-leverage opportunities to apply AI — this is a support function, so success means other teams shipping faster because of what you've built
• Establish the guardrails, review practices, and documentation that make AI-generated code safe to ship, and act as the internal advocate who helps teams adopt good practices without mandating a single tool
• Track adoption and measure the real impact of AI tooling on velocity and quality, and report back to leadership

Preferred

• 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
• Developer Experience
• Platform Engineering
• Internal Tooling
• LLM Evaluation
• Coding Agent Benchmarking
• Go
• Rust
• Python
• Security Practices
• Code Review
• Developer Relations
• Technical Evangelism
• Developer Advocacy
• Internal AI Adoption
• Technical Project Management
• Analytical Reasoning

Benefits

• An inclusive, flexible environment; flexibility in how and when you work.
• An equity incentive plan.
• Variable commission for quota-based roles.
• Comprehensive group benefits with no waiting period, including health, vision, dental, and other coverage for you and your family.
• Remote-first work; most teams work fully remotely. Some roles require in-office collaboration depending on team needs, as noted in the job description.
• Virtual and in-person social events and a corporate co-working program to visit WeWork or similar spaces nearby.
• Employer-funded retirement contributions: dollar-for-dollar matching of your retirement contributions, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.
• An annual company retreat, team off-sites, and support for intentional in-person connection through team travel and distributed collaboration.
• $1,500 USD annually for professional development, or mentorship, coaching, and internal promotion opportunities.
• Flexible paid time off.
• A company-owned laptop of your choice (Mac or PC), a monthly home internet reimbursement, and $500 USD to customize your workstation.
• Paid parental leave top-ups: 20 weeks for birthing parents and 16 weeks for non-birthing parents.

Company

• Zero-trust secure connectivity platform for dev, IT, and security teams
• Toronto, Ontario, CAN
• https://www.tailscale.com/
• Founded in 2019
• 201-500 employees

Qualifications

• 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
• 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
• 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

Required skills

• AI Coding Tools Claude Code, AI Coding Tools Codex, AI Coding Tools Pi, Code Review, Developer Experience, Developer-Facing Automation, Go, Internal Tool Development, LLM Evaluation and Benchmarking, Platform Engineering, Python, Rust, Security, Technical Project Management

Preferred skills

• Experience evaluating or benchmarking LLMs and coding agents, Technical project management experience

Experience

• 5+ years