Leadership Development Specialist

Clutch Technologies Inc.; Canada; On-site; CAD 80,000 - 100,000; Full time

Job summary

A leading online car retailer in Canada is seeking a Leadership Development Specialist to design and deliver impactful leadership programs. The role involves partnering with HR and teams to identify gaps and create scalable development experiences. Ideal candidates will have 3–7+ years in leadership development and strong facilitation skills. This position offers an opportunity to shape future leaders within a growing organization, contributing to a culture of continuous improvement.

Qualifications

• 3–7+ years of experience in leadership development, OD, learning & development, or talent management.
• Proven experience designing and facilitating leadership programs for multiple levels.
• Coaching certification or formal coaching training (ICF, Co‑Active, ORSC, etc.).

Responsibilities

• Design and lead scalable leadership development programs for emerging, mid-level, and senior leaders.
• Partner with HRBPs to assess leadership needs and align programs to business priorities.
• Define success metrics for programs and track trends in leadership capability.

Skills

Leadership development

Facilitation skills

Project management

Change management

Job description

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, visitclutch.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.

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.
• 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.