D2L is a cloud company that is modernizing education and building the Future of Work. The old models of teaching and learning are in the midst of the largest transformation in history, and D2L is at the heart of that fundamental shift.

New models of teaching and learning enable a personalized, student-centric experience – and deliver improved retention, engagement, satisfaction, and results for learners of all ages – in schools, campuses, and companies.

D2L is disrupting the way the world learns, by providing the next generation learning environment and solutions to engage and inspire learners. And most importantly, by giving customers a platform that is easy, flexible, and smart. No other company provides a solution as robust and innovative as D2L.

D2L has had a singular mission for 25 years and is dedicated to that same mission in the years ahead: to transform the way the world learns – and by doing so, we will help improve human potential globally.

Every application we receive is personally reviewed by a member of our Talent Acquisition team - yes, a real person looks at your resume While we use AI tools internally to streamline tasks like meeting notes, summaries, and administrative work, these tools never rank resumes, make hiring decisions, or influence candidate evaluations.

Job Summary

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.

How will I make an impact?

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 transparent business out

📌 Senior Transformation Director (Toronto)
🏢 D2L
📍 Toronto