Instructional Designer, AI-Augmented Learning Strategy

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 an Instructional Designer, AI-Augmented Learning at Redwood, you'll play a critical role in translating complex technical content into structured, engaging learning experiences for customers and internal teams. Working closely with a Senior Instructional Designer, Content Developers, and subject matter experts (SMEs), you'll support the full development lifecycle for training programs across Redwood's automation and file transfer platforms.

You're highly organized, detail-oriented, and fluent in using AI tools to accelerate and elevate your work. This role directly contributes to customer onboarding, product adoption, and overall learning effectiveness.

Instructional Design & Content Development

• Own the instructional design lifecycle from needs analysis through development and evaluation, applying frameworks such as ADDIE, SAM, and Bloom's Taxonomy
• Structure content into clear, modular lessons with knowledge checks and assessments that include targeted, actionable feedback
• Utilize structured AI workflows to transform reference materials into structured learning assets, identifying gaps and iteratively refining interactive eLearning, video and guides.
• Design and maintain AI-assisted content development workflows, including structured pipelines for SME synthesis and content generation, AI-generated draft storyboards, AI narration and script generation, and automated review passes
• Document reusable AI workflows, skills and knowledge resources so processes scale across the team

Storyboarding & Action Mapping

• Lead action mapping exercises to align learning content with business goals and performance outcomes, then translate those into detailed storyboards that define instructional flow, interactivity, and asset requirements
• Leverage AI tools to accelerate storyboard drafting, generate scenario variations, and prototype interactive learning flows
• Evaluate and integrate emerging AI tools (including generative video, AI voice and narration, and adaptive learning scaffolding) against content quality standards; own the decision log for when and how AI-generated assets enter the production pipeline
• Partner with Content Developers to align on design intent and support development in Articulate Rise, Storyline, Camtasia, and Review 360

SME Coordination

• Coordinate with subject matter experts to gather content, validate accuracy, and maintain scope alignment
• Communicate timelines, expectations, and deliverables to SMEs; provide guidance on content structure, best practices, and templates
• Apply structured AI workflows to process raw SME input (e.g., call recordings, rough documentation, or interview notes) into draft lesson content: this includes prompt design, output validation, and SME review handoff, not one-off copy-paste from a chat window

Content Workflow, Tools & LMS

• Work within established workflows across Atlassian, Google Drive, and authoring tools; maintain adherence to team standards, naming conventions, and file structures
• Perform routine LMS administration within Redwood University to support content organization, updates, and system accuracy
• Facilitate review cycles using Articulate Review 360; track, document, and resolve feedback from SMEs, Product, and stakeholders
• Ensure content meets quality, accuracy, and usability standards prior to release
• Maintain and update existing learning content in response to product changes, learner feedback, and post-project reviews

YOUR EXPERIENCE

Required 

• 5+ years in instructional design or learning experience design
• Experience with eLearning authoring tools (Articulate Rise, Storyline, Camtasia)
• Demonstrated ability to translate complex technical content into structured, learner-appropriate formats
• Experience creating storyboards and instructional design documentation
• Applied knowledge of adult learning theory in production content design
• Demonstrated AI fluency in a production learning context: be prepared to describe a specific workflow you designed and operated, what it replaced, and what you measured. Occasional tool use does not meet this bar
• Experience designing training for SaaS, enterprise software, or technical products

Preferred

• Experience with agile frameworks (Scrum, Kanban) in a collaborative development context
• Experience with LMS platforms and SCORM-based content delivery
• Experience with learning analytics and assessment design best practices

Pay Transparency:  The typical base salary range for this position is 67,000 - 84,000 CAD 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.

Vacancy Status : Existing vacancy

AI Transparency Disclosure: 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; all final hiring and selection decisions are made exclusively by individuals on the hiring team.

If you like growth and working with happy, enthusiastic over-achievers, you'll enjoy your career with us!

THE LEGAL BIT
Redwood 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 job-boards.greenhouse.io