Leadership Development Specialist

Clutch Canada; Toronto; On-site; CAD 80,000 - 100,000; Full time

Job summary

A leading online used car retailer in Toronto is seeking a Leadership Development Specialist to design and deliver programs aimed at fostering high-performing leaders. You will collaborate with HR and management to bridge leadership capability gaps and create impactful development experiences. The role requires strong facilitation skills and a background in leadership initiatives. Join us to shape a culture of leadership excellence and contribute directly to our organizational growth.

Benefits

Competitive compensation

Comprehensive benefits

Opportunities for leadership exposure

Qualifications

• 3–7+ years of experience in leadership development or talent management.
• Proven experience designing and facilitating leadership programs for multiple levels.
• Strong project management skills with the ability to manage multiple programs.

Responsibilities

• Design and lead scalable leadership development programs for all leader levels.
• Facilitate engaging training sessions using adult-learning methods.
• Define success metrics for programs and refine based on feedback.

Skills

Leadership development

Strong facilitation skills

Project management

Coaching certification

Change management

Familiarity with DEI-centered leadership

Job description

About Clutch:

We’re on a mission to reinvent the way people buy, sell, and own cars. Are you game?

Clutch is Canada’s largest online used car retailer, delivering a seamless, hassle-free car-buying experience to drivers everywhere. Customers can browse hundreds of cars from the comfort of their home, get the right one delivered to their door, and enjoy peace of mind with our 10-Day Money-Back Guarantee… and that’s just the beginning.

Named two years in a row to the Globe & Mail’s list of the Top Growing Companies in Canada and also awarded spots on Deloitte’s Technology Fast 50™ and Fast 500™ lists, we’re looking to add curious, hard-working, and driven individuals to our growing team.
Headquartered in Toronto, Clutch was founded in 2017 and currently services Ontario, New Brunswick, Nova Scotia, British Columbia, and Prince Edward Island. Clutch is backed by a number of world-class investors, including D1 Capital, Canaan, Real Ventures, BrandProject, and Upper90. To learn more, visit clutch.ca.

About the Role

We’re looking for a Leadership Development Specialist to design, deliver, and continuously improve leadership programs that build strong, inclusive, and high-performing leaders across the organization. In this role, you’ll partner with HR Business Partners, manager and cross-functional teams to identify leadership capability gaps, create development experiences, and measure impact.

You’re equal parts strategist and builder: comfortable crafting frameworks, facilitating workshops, coaching leaders, and using data to evolve what “great leadership” means here.

What You’ll Do

Program Design & Delivery

• Design and lead scalable leadership development programs for emerging, mid-level, and senior leaders.
• Create learning journeys that blend workshops, cohorts, self-paced content, peer learning, and on-the-job practice.
• Facilitate engaging training sessions (virtual and in-person) using adult-learning and experiential methods.
• Build manager enablement tools (guides, playbooks, templates, microlearning).

Talent & Organizational Development

• Partner with leadership and HRBPs to assess leadership needs and align programs to business priorities.
• Support high-potential development initiatives.
• Integrate leadership competencies into performance, career development, and change initiatives.
• Contribute to organizational culture programs that reinforce values and expected leadership behaviors.

Measurement & Continuous Improvement

• Define success metrics for programs (participation, behavior change, business impact).
• Collect qualitative and quantitative feedback and use insights to refine programming.
• Track trends in leadership capability and recommend improvements based on data and best practices.

What We’re Looking For

• 3–7+ years of experience in leadership development, OD, learning & development, or talent management.
• Proven experience designing and facilitating leadership programs for multiple levels.
• Strong facilitation and group dynamics skills (both virtual and in-person).
• Ability to translate business goals into leadership capability frameworks and development plans.
• Experience using assessment tools (e.g., 360s, psychometrics, engagement data) to guide development.
• Strong project management skills with the ability to manage multiple programs.
• Coaching certification or formal coaching training (ICF, Co-Active, ORSC, etc.).
• Experience with change management and organizational transformation.
• Familiarity with DEI-centered leadership development.
• Experience in high-growth environments.
• Knowledge of LMS/LXP platforms and modern learning tech.

Why you’ll love it at Clutch:

• You’ll have broad and direct ownership over talent acquisition strategy during a phase of rapid growth.
• Opportunity to build your team, your tools, and influence company culture and workforce at every level.
• Exposure to senior leadership, ability to contribute to major strategy, not just execution.
• Competitive compensation, benefits, and chance to work in a culture that values innovation and impact.

Clutch is committed to fostering an inclusive workplace where all individuals have an opportunity to succeed. If you require accommodation at any stage of the interview process, please email [e-mail].