Remote opportunity at
TailscaleDocumentation Platform Engineer
Tailscale is seeking a full-stack Documentation Platform Engineer to help evolve its customer-facing documentation site into a comprehensive platform. Founded in 2019, the company builds software…
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About This Role
Tailscale is seeking a full-stack Documentation Platform Engineer to help evolve its customer-facing documentation site into a comprehensive platform. Founded in 2019, the company builds software designed to simplify secure connections and network protection for users ranging from individual hobbyists to large multinational corporations. In this fully remote position, you will own the tools, publishing pipelines, API documentation, and search capabilities used by internal teams, customers, and external contributors. You…
Job Description
Tailscale is seeking a full-stack Documentation Platform Engineer to help evolve its customer-facing documentation site into a comprehensive platform. Founded in 2019, the company builds software designed to simplify secure connections and network protection for users ranging from individual hobbyists to large multinational corporations.
In this fully remote position, you will own the tools, publishing pipelines, API documentation, and search capabilities used by internal teams, customers, and external contributors. You will collaborate closely with product, design, growth, and engineering groups to build scalable infrastructure capable of serving millions of monthly visitors while supporting modern documentation trends like large language models and docs-as-code workflows.
Responsibilities
- Develop and enhance the documentation site to deliver an educational and seamless experience for developers, enterprises, and homelabbers.
- Manage and scale docs-as-code publishing pipelines for internal and external contributors.
- Collaborate cross-functionally with engineering and product teams to integrate documentation platforms with core software.
- Partner with design, research, and growth teams to bring experimental features into production.
- Build and optimize search and discovery tools for human visitors and automated agents.
- Engage with open-source contributors through GitHub issues, pull requests, and discussions.
- Track platform performance to ensure high scalability for millions of monthly users.
Requirements
- Experience building, deploying, and maintaining documentation sites using static site generators or tools like Hugo, Docusaurus, NextJS, or Astro.
- Familiarity with docs-as-code publishing workflows and their impact on user adoption.
- Proficiency in JavaScript, TypeScript, and React.
- Working knowledge of Python, command-line interfaces, shell scripting, and Git.
- Ability to implement designs using modern HTML and CSS.
- Experience setting up CI/CD pipelines, automated testing, and automated content workflows.
- Understanding of the practical implications and applications of LLMs in development and content consumption.
Qualifications
- Previous open-source contribution experience involving GitHub issues and pull requests.
- Understanding of how large language models interact with documentation.
- Familiarity with multi-format content outputs such as Markdown, HTML, JSON, XML, PDF, and ePub.
Core Skills
Benefits
- Base salary ranging from USD 163,000 to 204,000 per year
- Equity incentive plan
- Comprehensive group benefits for health, vision, and dental with no waiting period
- Employer-matching retirement contributions up to 0.75 percent of eligible compensation
- Flexible paid time off program
- Annual professional development budget of USD 1,500
- Home office setup including a choice of Mac or PC laptop, monthly internet reimbursement, and a USD 500 workstation stipend
- Paid parental leave providing up to 20 weeks for birthing parents and 16 weeks for non-birthing parents
- Access to corporate co-working spaces and company retreats
Frequently Asked Questions
Answers are based only on the employer’s listing; where it doesn’t say, neither do we.
Is this a remote position?
Yes, Tailscale operates as a remote-first company where most teams work fully from home or remote locations.
What is the salary range for this role?
The target US base salary for this position ranges from $163,000 to $204,000 USD per year, with exact offers varying based on experience.
What additional compensation and perks are included?
The compensation package includes base salary, equity incentives, health and dental benefits, retirement matching, a professional development budget, a home office setup allowance, and paid parental leave.
What primary technical skills are required?
Candidates must have experience with documentation platforms or static site generators like Hugo, Docusaurus, NextJS, or Astro, along with proficiency in TypeScript, JavaScript, React, Python, Git, and CI/CD pipelines.
Sample Interview Questions
AI-generated questions tailored to this specific role — a preview of the full practice set.