Documentation Manager

  • Tailscale Inc.
  • Remote
  • May 22, 2021
Full-time Technical Writing Remote-Friendly

Job Description

We're seeking a talented and motivated individual to write and oversee product documentation at Tailscale. As the first team member in this dedicated role, you will: work closely with our users and our team to define a documentation roadmap; publish engaging content; and empower our customers to get started quickly.

Tailscale is a technical product. Good documentation makes it easy for everyone (from hobbyists to seasoned IT professionals) to use. Our documentation must be accessible, straightforward, comprehensive, and trustworthy to a wide audience.

You will:

  • Work with our product team to document new features and APIs
  • Organize documentation and make it easily discoverable
  • Achieve and maintain content quality through testing and review, as well as curation and performance analysis
  • Share feedback and collaborate with our product and growth teams to improve feature and documentation discoverability
  • Assess documentation success through metrics and qualitative analysis

You may be a good fit if:

  • You have a framework for listening to users
  • You’re creative, empathetic, collaborative, optimistic, and curious
  • You have a technical background in computer networking
  • You’re an excellent writer, perhaps with a bent towards product management
  • You’re a perpetual learner and teacher
  • You’re resourceful and thrive on a high level of autonomy and responsibility

It’s nice if you have:

  • Experience with user interface or interaction design
  • Experience creating automated documentation tools
  • Experience with information architecture projects

You should include these in your application:

  • Your resume
  • Any additional materials (e.g., writing sample in a particular style, description of why you want to work in this role, a paragraph describing relevant experience)


Tailscale is a fully remote company with employees in both Canada and the United States. We offer:

  • An endless stream of fun and interesting challenges in a small and quickly growing company
  • Flexible (and reasonable) working hours -- work/life balance is exceptionally important to us
  • Competitive compensation and stock options
  • Comprehensive medical/dental benefits
  • 4 weeks of paid vacation (standard across the company)
  • An allowance for equipment to help you personalize your workspace

This is a full-time position. Our team is spread across Toronto, Montréal, New York City, Seattle, San Francisco, Waterloo, Berkeley, Ottawa, Victoria, Phoenix, and elsewhere. We prefer someone based in Canada or the continental United States who can maintain several hours a day of overlap with the Eastern timezone.

Tailscale is proud to be an equal opportunity employer and is committed to building a work environment that is both diverse and inclusive. All qualified applicants will receive consideration for employment regardless of race, religion, gender, gender identity or expression, sex, sexual orientation, ethnicity, creed, color, national origin, marital status, disability, veteran status, genetic information, or age. Accommodations are available on request for candidates taking part in all aspects of the hiring process.

Only candidates selected for interviews will be contacted. No recruiters, please.