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Tailscale

Connects devices through encrypted private networks

Documentation Platform Engineer

Full-Stack EngineeringConfirmed live in the last 24 hours
Full-timeRemote in CanadaCA$218.4k - CA$273.4k

About the Job

Requirements

  • A proven track record of building, extending, maintaining, and deploying documentation sites using static site generators such as Hugo or Docusaurus, or documentation platforms built on NextJS, Astro, or similar tools.
  • Familiarity with a docs-as-code publication workflow and understanding of how documentation experience affects user awareness, adoption, and growth.
  • Fluency in TypeScript, JavaScript, and React, and comfort with Python, command-line interfaces, shell scripting, and Git.
  • Comfort with modern HTML and CSS and ability to implement designs provided by others.
  • 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.
  • Ability to explain the impact and implications of large language models (LLMs) as both tools for application development and consumers of published documentation.

Responsibilities

  • Continuously improve and evolve the documentation site to create a helpful, educational experience that helps homelabbers, developers, and enterprises and their agents get the most out of Tailscale products and features.
  • Maintain and expand docs-as-code tooling and content publishing pipelines so internal and external contributors can publish error-free content quickly.
  • Work cross-functionally with 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 modern search and discovery infrastructure so visitors and agents can find answers quickly.
  • Work with open-source contributors through GitHub discussions, issues, and pull requests.
  • Monitor platform performance and maintain scalability for millions of visitors per month.
  • Research, experiment, and measure results to stay ahead of documentation trends.

Desired Qualifications

  • Open-source experience and comfort engaging with contributors on GitHub issues and pull requests.
  • Understanding of how large language models consume and interact with documentation.
  • Understanding of multi-format content output, including HTML, JSON, XML, raw Markdown, PDF, and ePub.

About the Company

Tailscale

Connects devices through encrypted private networks

Tailscale connects people, servers, and applications through encrypted private networks, giving businesses and individuals access to resources across clouds and physical locations. Its software uses WireGuard to encrypt traffic and connects devices directly where network conditions allow, with encrypted relay paths for harder connections. Administrators use identity services and access policies to manage who reaches each resource, without exposing every system to the public internet. The company sells business subscriptions priced by seats, with additional controls for larger teams and a free plan for personal use. Founded in 2019, Tailscale is headquartered in Toronto, Ontario, Canada.

Company size
201-500
Company stage
Series C
Total funding
$275M
Headquarters
Toronto, Canada
Founded
2019

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