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Director, Customer Education & Documentation

redwoodsoftware · Toronto, Canada · Ontario, Canada
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<h3><em><strong>OUR MISSION</strong></em></h3> <p><strong>At Redwood, we empower our customers with lights-out automation for their mission-critical business processes.</strong></p> <h2> </h2> <h3><em><strong>ABOUT US</strong></em></h3> <p>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.</p> <h2> </h2> <h3><em><strong>CORE VALUES</strong></em></h3> <p>One Team. One Redwood<br>Make Your Own Weather<br>Obsess over Customer Success<br>Work the Problem<br>Be Curious<br>Own the Outcome<br>Respect Each Other</p> <h2> </h2> <h3><em><strong>YOUR IMPACT</strong></em></h3> <p><em><strong></strong></em></p> <p data-pm-slice="1 3 []">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.</p> <p> </p> <p>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.</p> <h4><strong>Reinvent the Team for AI</strong></h4> <ul> <li> <p>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.</p> </li> <li> <p>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.</p> </li> <li> <p>Build and run agentic pipelines for drafting, translation, release-note and change-driven updates, link and quality checks, and content-gap detection.</p> </li> <li> <p>Reskill current team members, reset role definitions and career paths, and hire selectively for the capabilities the redesigned team requires.</p> </li> <li> <p>Set measurable productivity and quality targets (cycle time from release to published content, coverage, accuracy, cost per asset) and report results.</p> </li> <li> <p>Make content structured and machine-readable so that customers, partners, and AI assistants can consume Redwood documentation reliably.</p> </li> </ul> <h4><strong>Build Best-in-Class Docs as Code</strong></h4> <ul> <li> <p>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.</p> </li> <li> <p>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.</p> </li> <li> <p>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.</p> </li> <li> <p>Raise API and developer documentation to the standard expected of a platform product, including OpenAPI-driven reference content.</p> </li> <li> <p>Establish quality, style, localization, and accessibility standards, and instrument documentation with usage and effectiveness analytics.</p> </li> </ul> <h4><strong>Drive In-Product Guidance and Onboarding</strong></h4> <ul> <li> <p>Own the Pendo guide strategy: in-app walkthroughs, tooltips, announcements, and contextual help that move new users to first value faster and reduce support demand.</p> </li> <li> <p>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.</p> </li> <li> <p>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.</p> </li> </ul> <h4><strong>Deliver Training That Changes Customer and Partner Outcomes</strong></h4> <ul> <li> <p>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.</p> </li&

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