Director, Customer Success Operations & Education

Director, Customer Success Operations & EducationToronto, Canada
OUR MISSIONAt Redwood, we empower our customers with lights-out automation for their mission-critical business processes.
ABOUT USRedwood 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 VALUESOne Team. One RedwoodMake Your Own WeatherObsess over Customer SuccessWork the ProblemBe CuriousOwn the OutcomeRespect Each Other
YOUR IMPACTAs 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 new 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, support deflection, and customer and partner satisfaction.
Lead a Global, Distributed Team
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, Professional Services, Marketing, and Partner teams to align content and training to the customer journey.
Present strategy, results, risks, and investment needs to senior executives.
YOUR EXPERIENCE
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. We weigh demonstrated outcomes over tenure;
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. If your background is elsewhere, show how you would build this capability or lead those who have it.
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 with API documentation and developer experience preferred.
Experience building revenue-generating education or certification offerings preferred.
Pay Transparency: 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 benefits, as applicable. Final compensation will be determined based on the candidate's skills, experience, and relevant qualifications.
If you like growth and working with happy, enthusiastic over-achievers, you'll enjoy your career with us!
THE LEGAL BITRedwood is an equal opportunity employer. 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. We also prohibit discrimination based on a perception that anyone has any of those characteristics or is associated with a person who has or is perceived as having any of those characteristics. 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. Should you wish for us to remove your personal data from our recruitment database, please email us directly at View email address on ca.hrm.tc
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