Head of Learning and Development

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.

A member of our Talent Acquisition team reviews ALL of our applications - yes a real person reviews resumes! They are excited to read more about what amazing things you could add to D2L.

D2L is undergoing a bold transformation—becoming a performance-driven, talent-dense, AI-enabled organization rooted in purpose and powered by people. As part of this evolution, we are seeking a strategic and experienced Head of Learning Development to lead the design and delivery of learning experiences that strengthen leadership, accountability, and growth at all levels of the organization.

Reporting to the Senior Director, Learning & Organizational Design, this individual contributor, senior-level role will focus on enabling leaders—from individual contributors to executives—by building a holistic leadership and self-leadership development strategy. You will play a key role in shaping how we develop our people in alignment with the D2L Way of Working, our enterprise-wide Change Framework, and our broader People & Culture strategy.

This role will collaborate closely with senior stakeholders, People & Culture partners, and business leaders across the company to create learning journeys that reinforce high performance, continuous growth, and cultural clarity.

Major Responsibilities (How Will I Make an Impact?):

Leadership Development Design & Execution

• 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.

Program Delivery & Facilitation

• 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.

Cultural and Change Enablement

• 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.

Collaboration and Influence

• 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.

Measurement & Impact

• 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.

Competencies (What you’ll bring to the role):

• 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.

Skills

• 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.

D2L Leadership Competencies

• 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

Skills and Recommended Experience:

• Bachelor’s or Master’s degree in Learning and Development, HR, Education, or a related field.

This role is ideally located in either Toronto or Kitchener, with a hybrid office policy that can be discussed during the interview process.

The expected base salary range for a new hire in this role is listed below. The annualized base salary offered is determined by each candidate’s relevant knowledge, skills, education, training and experience. It is aligned to ensure both internal and external competitiveness using market data for the geographic location and industry. As part of the total compensation at D2L the role may be eligible for additional benefits including a Wellness Subsidy, Equity Grants, Variable Incentive, and more.

Don’t meet every single requirement? We strongly encourage you to still apply! At D2L, we are committed to creating a diverse and inclusive environment. We encourage your application even if you don't believe you meet every single qualification outlined, because we love to help our people grow and develop!

Why we're awesome:

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 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.