Head of Learning and Development

Summary

Join D2L, a cloud company revolutionizing education and the Future of Work, as their Head of Learning Development. Reporting to the Senior Director, Learning & Organizational Design, you will lead the design and delivery of learning experiences that strengthen leadership, accountability, and growth at all levels. This senior-level role requires building a holistic leadership and self-leadership development strategy, collaborating with stakeholders, and creating learning journeys that reinforce high performance and cultural clarity. You will design and deliver impactful learning experiences, facilitate workshops, champion the D2L Change Framework, and define learning success metrics. The ideal candidate possesses proven experience in leadership development, strong instructional design skills, and a deep understanding of culture-building and change enablement. This role is ideally located in Toronto or Kitchener, offering a hybrid work policy.

Requirements

• Proven experience building and leading leadership development or learning programs in high-growth or transformation-focused environments
• Strong instructional design, facilitation, and content development skills across multiple modalities
• Experience enabling leadership development at various levels: ICs, new leaders, seasoned managers, and executives
• Deep understanding of culture-building, change enablement, and leadership accountability
• Demonstrated ability to collaborate cross-functionally and influence stakeholders across levels
• Familiarity with AI tools in learning, digital learning platforms (e.g., Brightspace), and data-informed learning practices
• Comfortable navigating complexity and ambiguity in a fast-paced SaaS or technology environment
• Deep learning and higher education experience
• Tech-savvy with a strong understanding of learning technologies and data analytics
• Strong project management skills with the ability to manage multiple initiatives concurrently
• Excellent communication and presentation skills, both written and verbal
• Leads by Example with personal and professional integrity, high accountability, and say/do ratio
• Boundaryless collaboration and influence skills both within team, peer group and broader organization. Effective communicator with a proven track record of success
• Delivers Awesome Outcomes: Strategic mindset and business acumen, with strong prioritization skills and a focus on organizational outcomes vs. team tasks. Effective problem solver, able to achieve results individually and through others, in fast paced, deadline-driven environments
• Talent Magnet: Talent-focused leader, with demonstrated ability to coach, build and lead a high performing, diverse team
• Better, Smarter, Faster: An agile learner, with a growth mindset, attention to detail and organizational skills. An operationally minded leader, with a focus on continuous improvement and innovation
• Wins Hearts and Minds: An effective communicator, with the ability to connect the why and the what. A change agent, with proven delegation, motivation, and team building skills
• Bachelor’s or Master’s degree in Learning and Development, HR, Education, or a related field

Responsibilities

• Lead the design and execution of a forward-looking leadership strategy that aligns to D2L’s evolving business needs and cultural aspirations
• Build a multi-level Leadership and Self-Leadership Series, including Leading Self, Leading Others, and Leading the Organization, embedded with the D2L Way of Working
• Integrate change management, AI fluency, and leadership accountability into all development offerings
• Design and deliver impactful, scalable learning experiences for leaders and high-potential ICs that emphasize clarity, feedback, accountability, coaching, and curiosity
• Facilitate engaging, high-quality leadership sessions and workshops that foster development across the business
• Leverage internal tools (Brightspace, Wave) and emerging best practices to enhance learning design and adoption
• Act as a champion of the D2L Change Framework, embedding its principles into leadership and team development programs
• Reinforce the evolving cultural identity through learning interventions that support performance, growth, and talent density
• Partner closely with Talent Enablement, P&C Business Partners, and senior leaders to diagnose development needs and deliver relevant, customized learning solutions
• Serve as an advisor and thought partner on leadership capability, learning culture, and talent readiness
• Define learning success metrics and leverage data to evaluate program effectiveness and continuously iterate
• Monitor trends in leadership development, learning science, and AI-enabled learning to ensure D2L remains future-ready

Benefits

• 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 Catch the Wave Program
• 2 Paid Days off for Catch the Wave 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 at our HQ in Kitchener, Winnipeg, Vancouver and Melbourne
• $110,000 — $130,000 CAD
• Wellness Subsidy
• Equity Grants
• Variable Incentive