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 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.
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.
Build and run agentic pipelines for drafting, translation, release-note and change-driven updates, link and quality checks, and content-gap detection.
Reskill current team members, reset role definitions and career paths, and hire selectively for the capabilities the redesigned team requires.
Set measurable productivity and quality targets (cycle time from release to published content, coverage, accuracy, cost per asset) and report results.
Make content structured and machine-readable so that customers, partners, and AI assistants can consume Redwood documentation reliably.
Build Best-in-Class Docs as Code Own the end-to-end documentation platform strategy: content in version control, authored in Markdown/MDX, built and published through CI/CD, reviewed through pull requests alongside product code.
Lead the migration from legacy authoring tools to a modern docs-as-code platform, including information architecture, content modeling, redirects, search, versioning, and access control.
Embed documentation in the product delivery lifecycle with engineering and Product: docs as a release gate, shared ownership, automated checks,



and documentation updates triggered by code and API changes.
Raise API and developer documentation to the standard expected of a platform product, including OpenAPI-driven reference content.
Establish quality, style, localization, and accessibility standards, and instrument documentation with usage and effectiveness analytics.
Drive In-Product Guidance and Onboarding Own the Pendo guide strategy: in-app walkthroughs, tooltips, announcements, and contextual help that move current users to first value faster and reduce support demand.
Partner with Product, Engineering, and Product Operations on tagging standards, guide governance, and analytics, so guides are resilient to product change and measured against adoption outcomes.
Connect in-product guidance, documentation, and training into one learning experience, so a user reaches the right content in the right place with no hand-offs.
Deliver Training That Changes Customer and Partner Outcomes Own the global customer education strategy and its delivery through Redwood University (Skilljar): role-based learning paths, certification, instructor-led and on-demand training, and partner and implementation-partner enablement.
Design onboarding programs for new customers and partners that measurably reduce time-to-value, ramp time, and onboarding-related support and services effort.
Use AI to scale course development, localization, personalization, and assessment, while holding a high bar for instructional quality.
Evaluate and, where the case supports it, build scalable and revenue-generating education offerings, including certification and partner programs.
Define and report education outcomes: completion, certification, adoption lift, onboarding time, suppor

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📌 Director, Customer Success Operations & Education (Ontario)
🏢 redwoodsoftware
📍 Ontario