Full-time Software Engineer, AI Enablement

Tailscale • United States

Remote

This Job is No Longer Active This position is no longer accepting applications

AI Summary

Tailscale is seeking a Software Engineer, AI Enablement to build tools, workflows, and practices that help engineers leverage AI-assisted development safely and effectively. The role involves defining and driving the internal AI-enablement roadmap, collaborating with engineering teams, and establishing guardrails for AI-generated code. Key requirements include 5+ years of software engineering experience and daily hands-on fluency with modern AI coding tools.

Key Highlights

Founding team member shaping AI enablement strategy

Direct impact on engineering velocity and safety

Partner with engineering leadership and Aperture team

Build internal tools and workflows for AI adoption

Key Responsibilities

Partner with engineering leadership and Tailscale's technical staff to define and drive the 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 tools, workflows, and shared practices that help engineers get real value from coding agents

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

Establish guardrails, review practices, and documentation that make AI-generated code safe to ship

Track adoption and measure the real impact of AI tooling on velocity and quality, and report back to leadership

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Technical Skills Required

Software Engineering AI Coding Tools Internal Tool Development

Benefits & Perks

Base salary

Equity incentive plan

Comprehensive benefits

Remote-first work environment

Employer-funded retirement contributions

Paid parental leave

Home office setup reimbursement

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Nice to Have

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

Experience in developer relations, technical evangelism, or customer-facing developer advocacy

Technical project management experience

Job Description

Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

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