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 recent 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 new 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 documentation, learning, and AI tooling, and make build-versus-buy recommendations. Partner with Product, Engineering, Customer Success, Support, Qualified Services, Marketing, and Partner teams to align content and training to the customer journey. Present strategy, results, risks, and investment needs to senior executives.

Bachelor's degree in a relevant field (Technical Communication, Instructional Design, Education, Engineering, Computer Science, Business, or similar); master's degree preferred. 10+ years of progressive experience in technical documentation, customer education, developer experience, technical content, or digital adoption for software products, including 5+ years leading managers and distributed teams. backgrounds in developer experience, documentation engineering, support knowledge management, and product-led onboarding are welcome. Demonstrated experience leading a team through a major change in how it works,



and delivering measurable gains in output, quality, or cost. Hands‑on fluency with AI in content production: you can describe specific workflows where AI generates content, what your team validates, how the tools fail, and how your approach has changed in the past six months.

Experience designing or governing agentic content workflows in production is strongly preferred. A docs‑as‑code platform you built or migrated to at scale (Git‑based workflows, Markdown/MDX, documentation platforms such as Mintlify, CI/CD publishing, automated content checks), and a record of working with engineering to make documentation part of the release process. You can state the size of the content estate, the team, and the results.

Experience leading teams in India and North America, with proven practices for distributed collaboration and consistent quality.

Strongly preferred: experience with Pendo or an equivalent digital adoption platform, including guide design, tagging and governance, and analytics‑based iteration.

Strongly preferred: experience running customer and partner training at scale, ideally on Skilljar or a comparable LMS, including certification and onboarding programs tied to adoption and time‑to‑value outcomes. Ability to define metrics, instrument programs, and show business impact to executives. Strong judgment about the trade‑off between speed and accuracy in content that customers rely on for mission‑critical systems.

Exceptional communication, stakeholder‑management, and executive presentation skills.

Background in automation, ERP, integration, or other technically complex enterprise software preferred.

Experience building revenue‑generating education or certification offerings preferred. The typical base salary range for this position is CAD $150,000 - $170,000 annually. The range represents base salary only, and does not include company bonus, incentive for sales roles, equity or advantages, as applicable.

As part of our commitment to hiring transparency and in compliance with Ontario law, please be advised that we utilize artificial intelligence (AI) tools during our interview process. Specifically, we may use an AI‑enabled notetaking assistant to help capture and summarize interview discussions. This tool is used solely to assist our hiring team in summarizing candidate information; THE LEGAL BIT

Redwood prohibits unlawful discrimination based on race, colour, religion, sex, gender identity, marital or veteran status, age, national origin, ancestry, citizenship, physical or mental disability, medical condition, genetic information or characteristics (or those of a family member), sexual orientation, pregnancy or any other consideration made unlawful by regional or local laws. All such discrimination is unlawful and will have a zero tolerance policy applied to it. Redwood will comply with all local data protection laws, including GDPR when it comes to the handling and processing of personal data.

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📌 Director, Customer Success Operations & Education (Toronto)
🏢 Redwood Software
📍 Toronto