Senior Transformation Director - D2L, Kitchener

About this opportunity

The Senior Transformation Director leads D2L's Artificial Intelligence Transformation Office program, which exists to change how D2L works by helping every team turn AI into real outcomes. This senior technology role builds literacy, confidence, and capability for teams to use AI effectively and responsibly.

The Senior Director owns D2L's 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.

Responsibilities

Make an impact through AI evangelism, literacy, enablement, portfolio ownership, governance, process and technology reimagination, and change management.

• 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.
• 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.
• 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.
• 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.

Who we're looking for

Candidates should bring extensive experience in business operations, process improvement, and enterprise transformation, coupled with strong technical depth.

• 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.
• Bachelor's degree or equivalent experience in Business, Operations, Technology, Organizational Development, or a related field.
• Working familiarity with current AI technologies, enterprise systems, workflow automation, and modern operating-model practices is preferred.
• Transformation, process improvement, change-management, agile, or project/program-management certification is considered an asset, including Lean Six Sigma, PMP, CSM, SAFe, or equivalent.