Director, Customer Education & Documentation
CA$150,000 – CA$170,000 / yr base salary
Posted 6 Oct 2026
BranchFactor Summary
The original posting with the fluff stripped out
- Expected experience
- 10+ yrs
- Management level
- People management
| Base salary | CA$150,000 – CA$170,000 / yr |
|---|
Field of studyBusiness, Computer Science, Education, Engineering, Instructional Design, Technical Communication (or related)
Study levelBachelor's or higher
OUR MISSION
At Redwood, we empower our customers with lights-out automation for their mission-critical business processes.
ABOUT US
Redwood Software is the leading orchestration platform for the autonomous enterprise, driving business transformation at the lowest total cost of ownership. Redwood empowers organizations to intelligently automate and orchestrate mission-critical business and IT processes across complex ERP, hybrid cloud, data and emerging agentic AI systems. Through its SaaS-first automation fabric—with AI embedded across the automation lifecycle—Redwood accelerates the path to autonomous operations. Backed by 30 years of experience and trusted by more than 50% of the Fortune 50, Redwood helps organizations unlock human potential to focus on innovation, growth and what’s next.
CORE VALUES
One Team. One Redwood
Make Your Own Weather
Obsess over Customer Success
Work the Problem
Be Curious
Own the Outcome
Respect Each Other
YOUR IMPACT
As Director, Customer Education & Documentation, you will lead Redwood's global documentation and customer education practice and rebuild it for an AI-first operating model. You will inherit an established team in Canada and India and reshape it: what the team produces, how it produces it, and how its impact is measured. AI-assisted and agentic content production, a best-in-class docs-as-code platform, in-product guidance through Pendo, and training that shortens time-to-value for new customers and partners are the four pillars of the role.
You are a builder and a player-coach at the system level. You set the strategy, then redesign the workflows, roles, and tooling that deliver it.
Reinvent the Team for AI
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Redesign the team's operating model, roles, and skills mix around AI-assisted and agentic content production, moving the team from writing and maintaining content by hand to designing, governing, and validating AI-generated content.
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Define which content work is delegated to AI, which stays with human judgment, and how validation is performed. Publish standards for accuracy, review, and provenance that the team follows.
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Build and run agentic pipelines for drafting, translation, release-note and change-driven updates, link and quality checks, and content-gap detection.
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Reskill current team members, reset role definitions and career paths, and hire selectively for the capabilities the redesigned team requires.