218K–273K CAD / year
Documentation Platform Engineer
FullstackRemote — Canada, United States, United Kingdom, Singapore
Published on 2026-11-03
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About this role
Build and evolve Tailscale’s customer-facing documentation platform, including its publishing pipelines, API documentation, and search. Improve how customers and contributors create, find, and use documentation at scale.
About the company
Tailscale builds a zero-config mesh VPN on WireGuard so teams can securely connect devices, servers, and cloud resources without traditional VPN complexity.
Stack
TypeScriptJavaScriptReactPythonHugoDocusaurusNext.jsAstro
What you'll do
- Improve the documentation site’s usability and educational experience
- Maintain docs-as-code tools and content publishing pipelines
- Integrate documentation with Tailscale’s platform
- Collaborate with design, research, growth, engineering, and product teams
- Improve search and content discovery, including for AI agents
- Engage with open-source contributors through GitHub
- Monitor performance and scalability for millions of monthly visitors
- Research and measure documentation improvements
What we're looking for
- Experience building and maintaining documentation sites with static site generators or web frameworks
- Familiarity with docs-as-code publishing workflows
- Fluency in TypeScript or JavaScript and React
- Comfort with Python, CLI tools, shell scripting, and Git
- Ability to implement designs using HTML and CSS
- Experience with CI/CD, automated testing, and content workflow automation
- Understanding of LLMs as development tools and consumers of published content
Nice to have
- Open-source experience and comfort engaging with GitHub contributors
- Understanding how LLMs consume and interact with documentation
- Experience publishing content in multiple formats, such as HTML, JSON, XML, Markdown, PDF, or ePub
Benefits
- Equity incentive plan
- Remote-first work and coworking program
- Retirement contribution matching up to 0.75% of eligible compensation
- Flexible paid time off
- Paid parental leave: 20 weeks for birthing parents and 16 weeks for non-birthing parents
- Annual professional development budget of $1,500 USD
- Company laptop, monthly internet reimbursement, and $500 USD home-office allowance
- Health, vision, and dental coverage with no waiting period