Learning Development Jobs in Ontario (NOW HIRING)

The SMB Enablement team supports the SMB Sales and marketing organization, including over 1,000 team members and partners, both in Canada and internationally. We drive the team member lifecycle experience-from onboarding and learning to growth, development, change management and channel readiness-ensuring our teams deliver excellent, consistent results for high performing sales teams.

Role Overview

The Senior Learning Specialist, reporting to the Manager, Marketing, leads the development of business-critical enablement learning programs for the SMB Sales Channel. You'll create and execute initiatives for sales excellence, new hire onboarding, continuous learning, and leadership development programs that foster growth, elevate team culture, and optimize performance.

This is an impact-focused, fast-moving role where you'll transform sales operations and execution by standardizing and delivering national sales training and designing live and asynchronous learning programs. You'll work cross-functionally with Marketing, Product, and Sales Operations to scale strategies and tactics that are valuable to sales teams-built for and developed with cross-functional partners.

We're looking for a passionate and experienced sales training and learning development expert with strong strategic thinking, high emotional intelligence, influential leadership qualities, and a proven ability to execute large-scale initiatives from conception to completion.

Learning Design & Curriculum Development

• Own end-to-end design of curricula aligned to business needs, translating objectives into practical, scalable learning solutions.
• Design and facilitate behavioral sales content, coaching programs, and live workshops that develop leadership capabilities and drive actionable results.
• Demonstrate sound instructional design practices that support effective learning transfer across diverse audiences.

Stakeholder Collaboration & Communication

• Build productive relationships with stakeholders at all levels, clarifying objectives and providing thoughtful recommendations throughout design and delivery.
• Facilitate virtual training, webinars, and 'train-the-trainer' sessions while executing flawless collaboration with Marketing, Product, and Sales Operations.
• Partner with stakeholders to reinforce learning methods and manage expectations professionally.

Measurement & Continuous Improvement

• Assess training needs using data insights and feedback, applying evaluation methods to measure learning effectiveness and connect outcomes to performance indicators.
• Conduct debriefs with stakeholders to identify successes and opportunities for improvement.
• Use feedback loops to continuously refine curriculum and delivery approaches.

Execution Excellence

• Manage learning initiatives with discipline, meeting timelines and quality expectations while coordinating multiple inputs and dependencies.
• Ensure documentation, materials, and reinforcement tools are accurate and complete, demonstrating accountability from design through implementation.
• Leverage learning tools and cutting-edge technologies (LMS, AI tools, google scripts) to deliver dynamic, engaging learning modules.

Capability Building & Mentorship

• Coach and mentor team members to support skill development, consistency, and professional learning standards.
• Share best practices, tools, and insights to strengthen team capability and demonstrate strong facilitation and advisory skills.
• Model continuous improvement and drive excellence across the enablement function.

• 5+ years of experience working cross-functionally in enterprise sales organizations, driving strategic decisions and implementing critical change through learning programs.
• Strong track record in Sales Training, Certification, and/or Sales Enablement with proven ability to design and deliver impactful learning solutions.
• Expertise in behavioural sales coaching and leadership development training.
• Strong live workshop design and facilitation skills with the ability to engage diverse audiences.
• Excellent communicator and proficient in training facilitation.
• Demonstrated ability to assess training needs, measure learning effectiveness, and continuously improve programs based on data and feedback.
• Bilingual in both French and English written and verbal communication is a required asset.

• Dynamic Communicator: Adept at navigating ambiguity and driving efficient outcomes through expert facilitation and presentation, adapting to diverse stakeholders.
• Analytical Thinker: Drives meaningful, data-driven decisions by effectively interpreting data, asking insightful questions, and connecting learning outcomes to business impact.
• Creative Designer: Skilled in compelling storytelling and impactful visual presentations using Google Workspace, prioritizing audience engagement and instructional design excellence.
• Resilient Performer: Thrives in fast-paced, ambiguous environments with a proactive and focused approach, maintaining quality and integrity under pressure.
• Strategic Partner: Builds productive relationships with senior leaders and stakeholders, influencing decisions and reframing problems to drive capability change.

Seasoned Skills & Experience

• Strong project management, innovation, and organizational abilities enabling effective strategic execution.
• Confident working with performance data, and developing compelling communications and presentations.
• Proficient with innovative digital technologies and experience with LMS and AI tools for behavioral coaching.
• Build strong, collaborative relationships and effectively communicate risks and opportunities to all levels of the sales organization.
• Ambitious and motivated individual who takes pride in getting the job done and 'leans in' to owning decision-making.
• Proven ability to coach and mentor team members to strengthen capability and consistency.

Great to Haves

• 3-5 years of experience in Learning & Development, Management Consulting or Corporate Strategy within a large organization.
• Background in telecommunications and digital transformation.
• Professional training certification and/or adult learning experience.
• Experience designing and delivering behavioural sales training and leadership coaching programs with proven results.
• Demonstrated expertise in experiential learning design and integrated LMS technologies.
• Track record of establishing learning standards or frameworks that persist and are adopted by others.

Why Join Us?

We're on the leading edge of digital learning transformation and sales excellence. 

We're energized by meaningful collaboration and having the confidence to deliver what we set out to achieve.

If our team and this role resonates with you, we encourage you to apply today!