Senior Transformation Director

The Senior Transformation Director leads D2L’s Artificial Intelligence Transformation Office (AITO) program, which exists to change how D2L works by helping every team turn AI into real outcomes — faster execution, better decisions, and less time spent on the mundane. The role builds the literacy, confidence, and capability for teams to use AI effectively and responsibly, moving pragmatically, keeping it simple, and making responsible use of AI the default.

The Senior Director owns D2L’s AITO portfolio end to end and leads through influence — partnering with functional leaders across the business and technical teams to reimagine how core processes and emerging technology will transform D2L’s approach to work. 

The Senior Director is accountable for the operational results of each initiative, measured in cycle time, cost to serve, quality, decision speed, and capacity returned to higher-value work. Process redesign and new technology are delivered as a single piece of work, since neither produces a result on its own. Functional teams lead the change in their own areas, supported by the method, patterns, and enablement this role provides, which keeps ownership and capability in the business after an initiative closes. 

AI Evangelism, Literacy, and Enablement 

• Develop AI literacy and capability across functions through enablement programs, cohorts, playbooks, office hours, and reusable patterns. 
• Make responsible use the default by building clear, simple guidance on appropriate use, data handling, and human oversight into everyday workflows  
• Establish reusable, governed design patterns for AI agents and use controlled review-and-improvement cycles to deliver reliable business outcomes more quickly. 
• Keep enablement and guidance current as internal tooling, platform capabilities, and the external AI landscape evolve. 
• Ensure every AI-enabled change carries the enablement, adoption, measurement, and support model needed to sustain it. 

Portfolio Ownership and Governance 

• Partner with various business unit leaders to uncover operational friction points, identify high-impact AI use cases, and consolidate these into a unified AITO roadmap that drives operational change across the organization. 
• Ensure work is measured by sustained business outcomes — revenue growth, profitability, increased output, time returned, cycle time, quality, decision speed, and real adoption — not only by activity or implementation milestones. 
• Report portfolio health, adoption, and realized value to the AITO Steering Committee and senior leaders on a regular cadence. 
• Conduct retrospectives and embed lessons learned into D2L’s transformation methods, practices, and standards. 
• Serve as the primary interface to the Senior Leadership team at D2L — bringing forward prioritization decisions, tradeoffs, capacity constraints, and risks, and carrying decisions back into the portfolio. 

Process and Technology Reimagination 

• Define the target technology footprint for each redesign, including where AI, automation, and integration are applied, what existing systems and services are extended, retired or consolidated. 
• Identify opportunities to simplify work, reduce manual effort, improve execution quality, and increase operational effectiveness. 
• Lead the redesign of business processes, workflows, roles, decision rights, and handoffs so future-state ways of working are practical and grounded in a clear business outcome. 
• Ensure future-state processes include clear ownership, documentation, adoption needs, and transition plans for steady-state ownership. 
• Partner with Information Technology, Security, Legal, and Privacy to ensure that solutions are responsible, supportable, secure, and aligned with D2L standards 

Change, Adoption, and Sustained Use 

• Apply a people-first change approach: involve affected teams in the design and give people the opportunity to forge how new ways of working take shape. 
• Support leaders and teams as they adopt new processes, tools, roles, and ways of working, and intervene where adoption stalls. 
• Use adoption feedback and lessons learned to improve future transformation work. 

• 10+ years of progressive experience leading, business operations, process improvement, organizational change, and enterprise transformation 
• Hands-on fluency with current AI tools, with enough technical depth to assess feasibility, effort, and risk credibly alongside technical partners. 
• Strong understanding of process redesign, operating-model change, adoption, and value realization. 
• Ability to translate strategic priorities into practical transformation plans and measurable outcomes. 
• Strong business acumen, systems thinking, judgment, and prioritization skills. 
• Exceptional ability to influence across functions and work effectively with senior stakeholders and executive governance bodies. 
• Practical orientation toward adoption, execution, and sustained business outcomes. 
• Experience supporting major enterprise change is considered an asset. 

At D2L, we are dedicated to providing you with the tools to do the best work of your life. While some of our perks and benefits may vary depending on location or employment type, we are proud to provide employees with the following through #LifeAtD2L:

• Impactful work transforming the way the world learns
• Flexible work arrangements
• Learning and Growth opportunities
• Tuition reimbursement of up to $4,000 CAD for continuing education through our SkillsWave Program
• 2 Paid Days off for SkillsWave-related activities like exams or final assignments
• Employee wellbeing (Access to mental health services, EFAP program, financial planning and more)
• Retirement planning
• 2 Paid Volunteer Days
• Competitive Benefits Package
• Home Internet Reimbursements
• Employee Referral Program
• Wellness Reimbursement
• Employee Recognition
• Social Events
• Dog Friendly Offices Spaces at our HQ in Kitchener, Winnipeg, Vancouver and Melbourne offices.