At Redwood, we empower our customers with lights-out automation for their mission-critical business processes. 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—for 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. At Redwood, we empower our customers with lights-out automation for their mission-critical business processes. 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—for 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. Obsess over Customer Success 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. 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. 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. Build and run agentic pipelines for drafting, translation, release-note and change-driven updates, link and quality checks, and content-gap detection. 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. 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. 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. Own the Pendo guide strategy: in-app walkthroughs, tooltips, announcements, and contextual help that move recent users to first value faster and reduce support demand. 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, support deflection, and customer and partner satisfaction. Lead managers and senior individual contributors in Canada and India, with a clear operating rhythm across time zones, shared standards, and consistent quality. Coach and develop leaders, set expectations, manage performance, and build succession. Manage the annual plan, budget, and vendor relationships for document

📌 Director, Customer Success Operations (Canada)
🏢 Redwood Software
📍 Canada