Job Overview
Location
Remote (United States)
Job Type
Full-time
Category
Writing
Date Posted
May 14, 2026
Full Job Description
đź“‹ Description
- • As a Technical Writer at Tailscale Inc., you will help create and deliver world-class product documentation, tutorials, conceptual guides, and examples that enable networking and security professionals and software engineers to understand when, why, and how to use Tailscale’s products and features. Your work will directly support customers in securely interconnecting people and devices across the globe, contributing to Tailscale’s mission of building a safer, simpler Internet.
- • Day to day, you will produce, test, and maintain technically accurate documentation using a docs-as-code workflow with Git, GitHub, and Markdown; develop how-to guides, reference materials, and tutorials tailored to diverse audiences including developers, infrastructure engineers, and security practitioners; collaborate with product managers, engineers, and subject-matter experts to plan and refine content; update documentation based on product changes and user feedback; support peers in improving their writing; and contribute to information architecture to improve content discoverability.
- • Tailscale is a fully remote, distributed company founded in 2019 and backed by Accel, CRV, Insight, Heavybit, and Uncork Capital. The company builds software that simplifies secure network connectivity for users ranging from hobbyists to multinational corporations, emphasizing ease, safety, and sensibility in internet access. The Documentation team plays a critical role in enabling user success and product adoption through clear, accurate, and accessible technical content.
- • In this role, you will deepen your expertise in networking and security technologies, become a trusted authority on Tailscale’s product suite, and grow your skills in technical communication, collaboration, and content strategy. You’ll have opportunities to influence documentation best practices, engage with the user community, and explore how LLMs and automation can enhance technical writing at scale.
🎯 Requirements
- • At least 3 years of professional technical writing and editing experience creating high-quality, code-heavy product documentation and how-to guides for a diverse technical audience
- • Technical proficiency with hands-on experience in networking or security products and comfort in technical conversations with engineers and product managers
- • Proficiency with Git, GitHub, Markdown, and command-line interface, including experience using a docs-as-code publishing workflow
- • Strong editing skills with the ability to guide others through writing processes and identify inconsistencies in tone, flow, and structure
- • Ability to drive multiple projects from start to completion while collaborating effectively with writers, editors, product managers, and subject-matter experts
- • Excellent written and verbal English communication skills, with openness to giving and receiving feedback
🏖️ Benefits
- • An inclusive, flexible remote-first environment that supports authentic self-expression and work-life integration
- • Competitive total compensation including base salary, equity, and variable commission (for quota-based roles)
- • Comprehensive group benefits with no waiting period, covering health, vision, dental, and more for employees and families
- • $1,500 USD annual professional development stipend, plus access to mentorship, coaching, and internal promotion opportunities
- • Paid time off program supporting any life situation, from relocation to travel
- • Build-your-own home office setup: choice of company-owned laptop (Mac or PC), monthly internet reimbursement, and $1,000 USD to customize your workstation
Skills & Technologies
About Tailscale Inc.
Tailscale Inc. provides a zero-config virtual private network built on the open-source WireGuard protocol. It creates secure, encrypted mesh networks that connect devices, servers and users without traditional VPN hardware or complex firewall rules. The software runs on Linux, macOS, Windows, iOS, Android and container platforms, integrating with identity providers like Google Workspace, Microsoft Entra ID and Okta. Organizations use Tailscale to enable remote access to internal applications, SSH, RDP, databases and development environments, while maintaining centralized access controls and audit logs. The company is privately held and headquartered in Toronto, Canada.
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