Software Engineer, AI Enablement

Tailscale

Software Engineer focusing on AI Enablement at Tailscale. Building tools and workflows for AI-assisted development in a remote setting.

Posted 7/24/2026full-timeRemote • 🇨🇦 CanadaMid-LevelSenior💰 CA$218,420 - CA$302,840 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in AI-enablement strategies, internal tool development, and effective communication across engineering and non-engineering teams. Proficient in evaluating AI models and implementing safe practices for AI-generated code.

Highest-signal resume keywords

5+ Years Software Engineering ExperienceHands-On Fluency With AI Coding ToolsInternal Tool DevelopmentStrong Communication SkillsProduct Or Systems Thinking

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Software EngineeringAI Model EvaluationInternal Tool DevelopmentAI-Generated Code PracticesAutomation

Soft Skills

Strong CommunicationInternal AdvocacyComfort With AmbiguitySelf-Directed Prioritization

Tools & Technologies

Claude CodeCodexPi

Industry Keywords

AI-EnablementEngineering VelocityQuality MeasurementHigh-Leverage Opportunities

About the role

Key responsibilities & impact

Partner with engineering leadership to define Tailscale's internal AI-enablement priorities and roadmap.
Work with the team that’s building Aperture by Tailscale – our AI gateway.
Build, maintain, and iterate on internal tools and workflows.
Evaluate new AI models, agents, and tools.
Work directly with both engineering and non-engineering teams to find opportunities to apply AI.
Develop infrastructure, guardrails, review practices, and documentation for the safe use of AI-generated code.
Act as an internal advocate for effective AI practices.
Track adoption and measure the real impact of AI tooling on engineering velocity and quality.
Expect the day-to-day to span hands-on building, teaching, and prioritization.

Requirements

What you’ll need

5+ years of professional software engineering experience
Genuine, daily, hands-on fluency with modern AI coding tools (Claude Code, Codex, Pi, or similar)
Experience building and shipping internal tools or developer-facing automation
Strong written and verbal communication and internal advocacy skills
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.

Benefits

Comp & perks

An inclusive, flexible environment where you can be your authentic self.
A competitive total compensation package.
Comprehensive group benefits with no waiting period.
Remote first company —most of our teams work fully remotely.
Employer-funded retirement contributions.
Connect with other Tailscalars IRL.
Support for your personal and professional development.
Paid time off and a healthy work-life integration.
A build-your-own home office setup.
Paid parental leave program.