Software Engineer, AI Enablement

About Tailscale

Tailscale simplifies secure online connections by developing software that enables users to safely link devices and people regardless of location. With a diverse user base ranging from hobbyists to global enterprises, Tailscale helps teams protect networks and access internal resources seamlessly. Founded in 2019 and fully remote, the company is supported by investors such as Accel, CRV, Insight, Heavybit, and Uncork Capital.

Role Overview

We are looking for a driven full-time Software Engineer to join our AI Enablement team. This critical role involves empowering our engineering organization with AI-powered development tools. Reporting to a co-founder and collaborating with the existing AI enablement engineer, you will design and implement tools, workflows, and practices that promote faster and safer development using AI. This foundational position offers substantial influence over the company's AI adoption strategy as we grow, with broad visibility across engineering teams.

Primary Responsibilities

• Collaborate with engineering leaders and technical staff to craft and execute the internal AI enablement roadmap.
• Work closely with the team developing Aperture by Tailscale, an AI gateway utilized internally and offered as a product.
• Create and refine tools, workflows, and standards that enable engineers to harness coding agents effectively; evaluate new AI models and tools to determine adoption suitability.
• Partner across engineering and other departments to identify impactful AI applications, supporting faster delivery through your solutions.
• Define safety guardrails, code review processes, and documentation to ensure safe deployment of AI-generated code, acting as an advocate for sound AI practices without enforcing a single tool.
• Monitor AI tooling adoption rates and assess their impact on productivity and quality, reporting insights to leadership.

Required Qualifications

• Minimum of 5 years professional software engineering experience.
• Intensive daily hands-on expertise with modern AI coding tools such as Claude Code, Codex, Pi, or equivalents—not just occasional usage.
• Experience designing and deploying internal tools or developer-focused automation.
• Excellent communication skills and ability to advocate internally, able to effectively teach and influence engineers with diverse AI experience levels.
• A balanced philosophy encouraging effective and secure AI use without mandates.
• Comfort thriving in an ambiguous environment with self-driven prioritization within a small, formative team.
• Product and systems thinking skills to identify high-value AI opportunities rather than merely executing predefined plans.

Preferred Qualifications

• Background in developer experience, platform engineering, or internal tooling.
• Experience assessing or benchmarking large language models (LLMs) and coding agents.
• Familiarity with systems programming languages like Go or Rust alongside Python.
• Knowledge of security or code review practices aiding evaluation of AI-generated code.
• Skills in developer relations, technical evangelism, or developer advocacy facilitating internal AI adoption.
• Technical project management experience.

Compensation & Benefits

• Competitive salary range for Canadian candidates from $218,420 to $302,840 CAD.
• Comprehensive compensation including base salary, equity incentives, and benefits.
• Inclusive and flexible work environment supporting authenticity and diverse perspectives.
• Extensive group benefits covering health, vision, dental, available immediately.
• Remote-first culture with optional in-person collaboration and corporate co-working programs.
• Employer-matched retirement contributions up to 0.75% of eligible income annually.
• Opportunities for in-person connections including annual retreats and team offsites across multiple countries.
• Professional development support with $1500 USD annual allowance, mentoring, coaching, and career growth paths.
• Flexible paid time off accommodating various life circumstances.
• Customizable home office setup with choice of company laptop, monthly internet reimbursement, and $500 USD for workstation personalization.
• Paid parental leave with top-ups: 20 weeks for birthing parents, 16 weeks for non-birthing parents.

Additional Information

Tailscale encourages applicants from underrepresented groups, aiming to reduce barriers common in job application processes. We prioritize fair and equitable hiring practices. The recruitment process includes AI-assisted screening tools, but all hiring decisions are made by people. For accommodations during hiring, contact your recruiter. Official communications come from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io domains. Beware of impersonation attempts.