Documentation Platform Engineer

Remote (Canada)RemoteFull-timeCA$218k–CA$273k2026-11-03 → 2026-11-10

Core

Build, maintain, and evolve a customer-facing documentation platform and tools for internal teams and external contributors to showcase Tailscale's products.

Role type

Senior full-stack Documentation Platform Engineer

Builds

Documentation site, content pipelines, API documentation, and search infrastructure

Domain

Developer tools / Documentation platforms

Required skills

TypeScript, JavaScript, React, Python, shell scripting, Git, HTML, CSS, static site generators (Hugo, Docusaurus, NextJS, Astro), CI/CD pipelines, automated testing, LLM integration

Preferred skills

Open source engagement, multi-format content output (HTML, JSON, XML, Markdown, PDF, ePub)

Responsibilities

Evolve documentation site for user experience; maintain docs-as-code tooling and publishing pipelines; integrate documentation with platform; partner with designers and growth teams; tune search and discovery infrastructure; manage open source contributor interactions; monitor platform performance and scalability

Seniority

Senior, hands-on IC

About Tailscale

Tailscale is building the new Internet 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.