[Hiring] Documentation Platform Engineer @Tailscale

Role Description

We're looking for an experienced full-stack Documentation Platform Engineer to evolve our documentation site into a platform that delivers an exceptional experience for Tailscale's prospective and current customers. You'll build, maintain, evolve, and support the platform and tools that internal teams and external contributors use to showcase Tailscale's features and products. This includes the documentation platform itself, our content pipelines, API documentation, and search. You'll work on a highly-visible customer-facing documentation site and you'll influence how documentation gets created, published, and consumed.

Key Responsibilities

• Continuously improve and evolve our documentation site to create a helpful, delightful, and educational experience that helps homelabbers, developers, and enterprises (and their agents) get the most out of Tailscale's products and features.
• Maintain and expand our docs-as-code tooling and content publishing pipelines, ensuring a smooth experience for both internal and external contributors to publish error-free content quickly.
• Work cross-functionally with other engineering and product teams to integrate documentation with the Tailscale platform.
• Partner with designers, user research, and growth teams to implement designs and features as they move from experimentation to production.
• Help shape and tune a modern search and discovery infrastructure to help visitors, and agents, discover answers quickly.
• Work with open source contributors through GitHub discussions, issues, and pull requests.
• Monitor the platform's performance and maintain scalability for millions of visitors per month.
• Stay ahead of documentation trends through research, experimentation, and measuring results.

Qualifications

• You have a proven track record of building, extending, maintaining, and deploying documentation sites using static site generators like Hugo or Docusaurus, or documentation platforms built on NextJS, Astro, or other similar tools.
• You are familiar with a docs-as-code publication workflow, and you understand the impact that a good documentation experience has on user awareness, adoption, and growth.
• You are fluent in TypeScript / JavaScript and React, and are comfortable with Python, command-line interfaces, shell scripting, and Git.
• You are comfortable with modern HTML and CSS and can implement designs provided by others.
• You have experience with CI/CD pipelines, automated testing, and automation for content or documentation workflows to reduce repetitive tasks and provide real-time feedback to authors.
• You can explain the impact and implications of LLMs as both tools for application development, and as consumers of content that documentation sites publish.

Nice to Have

• You have open source experience and are comfortable engaging with contributors on GitHub issues and pull requests.
• You understand how LLMs consume and interact with documentation.
• You understand multi-format content output (HTML, JSON, XML, raw Markdown, PDF, ePub).

Requirements

• US Pay Range: $163,000 — $204,000 USD

Benefits

• An inclusive, flexible environment where you can be your authentic self.
• A competitive total compensation package including base salary, equity incentive plan, and variable commission (for quota-based roles).
• Comprehensive group benefits with no waiting period, including health, vision, dental, and more for you and your family!
• Remote first company with most teams working fully remotely.
• Employer-funded retirement contributions with a dollar-for-dollar match, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.
• Connect with other Tailscalars IRL through annual company retreats and team off-sites.
• Support for your personal and professional development with $1500 USD annually for professional development.
• Flexible, paid time off program supporting any situation life throws your way.
• Build-your-own home office setup with a company-owned laptop and a $500 USD workstation customization budget.
• Paid parental leave program with top-ups for new parents.