Documentation Platform Engineer

Thank you for considering Tailscale. If this job description resonates with you, please apply. Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic! About Tailscale Tailscale is making safe connection effortless 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. About the Role 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 of 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. What We Are Looking For • 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 As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale's compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire's base salary. Individual offers may vary based on experience and skill set. CAN Pay Range $218,420—$273,360 CAD What We Offer • An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life. • A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles). • Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family! • Remote first company—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description. • Employer-funded retirement contributions. Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation. • Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration. • Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development,