Software Engineer, AI Enablement

About the role

Tailscale is seeking a Software Engineer to join a high-leverage team focused on AI enablement. You will build the tools, workflows, and practices that help the engineering organization utilize AI-assisted development safely and effectively. This foundational role involves shaping the company's AI strategy and measuring the impact of AI tooling on engineering velocity and quality.

Responsibilities

• Partner with engineering leadership to define and drive the internal AI-enablement roadmap.
• Build and iterate on tools, workflows, and shared practices for coding agents.
• Evaluate new models and tools to determine adoption.
• Partner with teams to identify high-leverage opportunities for AI application.
• Establish guardrails, review practices, and documentation for safe AI-generated code usage.
• Track adoption and measure the impact of AI tooling on velocity and quality.

Required skills

• Software Engineering
• AI coding tools
• Internal tools development
• Developer-facing automation
• Technical communication
• Systems thinking

Nice to have

• Developer experience
• Platform engineering
• LLM benchmarking
• Go
• Rust
• Python
• Security
• Technical evangelism
• Technical project management

Benefits

• Health insurance
• Vision insurance
• Dental insurance
• Retirement contributions
• Professional development budget
• Paid time off
• Home office setup
• Home internet reimbursement
• Paid parental leave

About the Company

Tailscale makes safe connection effortless by delivering software that allows users to securely interconnect people and their devices. Founded in 2019 and fully distributed, the company is backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.