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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.
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.
- 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.
- 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.
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, or take advantage of mentorship, coaching, and internal promotion opportunities.
- Paid time off and a healthy work-life integration. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!
- A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.
- Paid parental leave program. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).
Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.
Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.
Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.
Skills Required
- Proven experience building, extending, maintaining, and deploying documentation sites using Hugo, Docusaurus, Next.js, Astro, or similar platforms
- Familiarity with docs-as-code publication workflows and documentation’s impact on user awareness, adoption, and growth
- Fluency in TypeScript or JavaScript and React
- Comfort with Python, command-line interfaces, shell scripting, and Git
- Experience with modern HTML and CSS and the ability to implement designs provided by others
- Experience with CI/CD pipelines, automated testing, and content or documentation workflow automation
- Ability to explain the impact and implications of LLMs as application-development tools and consumers of documentation content
- Open-source experience and comfort engaging with contributors through GitHub issues and pull requests
- Understanding of how LLMs consume and interact with documentation
- Understanding of multi-format content output, including HTML, JSON, XML, Markdown, PDF, and ePub
Tailscale Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Tailscale and has not been reviewed or approved by Tailscale.
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Fair & Transparent Compensation — Pay is framed as market-competitive across functions and geographies, with compensation bands and ranges frequently described in concrete terms. Salary-range transparency is also emphasized through openly posted ranges and an “equitable total rewards” positioning.
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Leave & Time Off Breadth — Time off is positioned as flexible, with paid holidays and an extended year-end closure window highlighted. This breadth is presented as enabling meaningful disconnect time rather than narrowly defined PTO only.
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Parental & Family Support — Paid parental leave is described as substantial, including top-ups for an extended period. Family-inclusive health benefits with immediate eligibility are also positioned as supportive for dependents.
Tailscale Insights
What We Do
For teams who want secure, private networks without weeks of setup and configuration, Tailscale makes it easy. Unlike existing corporate VPNs, Tailscale has no upfront cost, minimal latency, and works with their existing services.
