4 hours ago
Remote, CanadaSenior
Responsibilities
- Improve and evolve Tailscale’s customer-facing documentation site and user experience.
- Maintain and expand docs-as-code tooling and content publishing pipelines for internal and external contributors.
- Integrate documentation with the Tailscale platform in collaboration with engineering and product teams.
- Implement designs and features with designers, user research, and growth teams.
- Develop and tune search and discovery infrastructure for documentation visitors and agents.
- Engage with open-source contributors through GitHub discussions, issues, and pull requests.
- Monitor platform performance and maintain scalability for millions of monthly visitors.
- Research documentation trends, run experiments, and measure results.
Requirements
- Proven experience building, extending, maintaining, and deploying documentation sites with tools such as Hugo, Docusaurus, NextJS, or Astro.
- Familiarity with docs-as-code publication workflows and the effect of documentation on awareness, adoption, and growth.
- Fluency in TypeScript or JavaScript and React, with comfort using Python, command-line interfaces, shell scripting, and Git.
- Ability to implement designs using modern HTML and CSS.
- Experience with CI/CD pipelines, automated testing, and automation for content or documentation workflows.
- Ability to explain how LLMs can support application development and consume documentation content.
- Open-source experience and comfort working with GitHub issues and pull requests are preferred.
- Understanding of how LLMs consume documentation and of multi-format outputs such as HTML, JSON, XML, raw Markdown, PDF, and ePub are preferred.
Benefits
- Remote-first, flexible work environment with access to virtual and in-person social events and a corporate coworking program.
- Base salary, equity incentive plan, and variable commission for quota-based roles.
- Comprehensive health, vision, dental, and other group benefits with no waiting period.
- Employer-funded retirement contributions matching employee contributions dollar-for-dollar up to 0.75% of eligible compensation.
- Annual company retreat, team off-sites, and support for distributed collaboration across Canada, the United States, the United Kingdom, and Singapore.
- $1,500 USD annually for professional development plus mentorship, coaching, and internal promotion opportunities.
- Flexible paid time off and paid parental leave of 20 weeks for birthing parents and 16 weeks for non-birthing parents.
- Company-owned laptop choice, monthly home internet reimbursement, and $500 USD for workstation customization.
Tech Stack
Categories
About Tailscale
Tailscale builds a software-defined mesh VPN that lets individuals and organizations securely connect devices and services using WireGuard and single sign-on. It sells a subscription SaaS with free and paid plans, offering features like access control lists, device authentication, and admin tooling for teams and enterprises. Founded in 2019 and headquartered in Toronto, the company is privately held and used from hobby projects to corporate networks.