Job Overview
Location
Remote (Canada)
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 play a critical role in making complex networking and security technology accessible to a global audience of developers, engineers, and IT professionals by creating clear, accurate, and user-focused documentation.
- • Day to day, you will produce, test, and maintain high-quality product documentation including how-to guides, conceptual topics, reference materials, and tutorials; collaborate with product managers, engineers, and subject-matter experts; refine content based on user feedback and metrics; support peer contributors in improving their writing; and contribute to information architecture to enhance content discoverability.
- • Tailscale is a fully remote, fast-growing company building innovative software that simplifies secure network connectivity for users ranging from individual developers to large enterprises, backed by top-tier investors and committed to an inclusive, engineering-driven culture.
- • In this role, you will deepen your expertise in modern networking and security technologies, refine your technical communication skills for diverse audiences, influence product usability through documentation, and grow professionally within a team that values documentation as a core part of the customer experience.
🎯 Requirements
- • At least 3 years of professional technical writing and editing experience creating code-heavy product documentation for technical audiences
- • Hands-on experience with 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 with docs-as-code publishing workflows
- • Strong editing skills with ability to guide others through writing processes and identify inconsistencies in tone, flow, and structure
- • Ability to manage multiple projects from start to finish while collaborating effectively with writers, editors, PMs, and SMEs
- • Excellent written and verbal English communication skills, with openness to giving and receiving feedback
🏖️ Benefits
- • Inclusive, flexible remote-first environment supporting 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
- • Generous parental leave top-ups for up to 26 weeks from day one
- • Build-your-own home office setup: company-owned laptop (Mac or PC), monthly internet reimbursement, and $1,000 USD for workstation customization
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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