Leadership Development Specialist

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 are seeking a Leadership Development Specialist to design, deliver, and continuously improve programs that develop strong, inclusive, and high-performing leaders across Clutch. You’ll partner with HR Business Partners, managers, and cross-functional teams to identify leadership capability gaps, create tailored development experiences, and measure program impact. This role balances strategy and hands-on execution, from building frameworks and facilitating workshops to coaching leaders and using data to guide improvements.

What you’ll do:

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Design and deliver scalable leadership programs for emerging, mid-level, and senior leaders.

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Create leadership learning journeys that blend workshops, cohorts, self-paced content, peer learning, and on-the-job practice.

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Facilitate engaging training sessions, both virtual and in-person, using adult-learning and experiential methods.

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Build manager enablement tools, including guides, playbooks, templates, and microlearning content.

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Partner with leadership and HRBPs to assess leadership needs and align programs to business priorities.

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Support high-potential development initiatives and integrate leadership competencies into performance, career, and change programs.

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Contribute to organizational culture initiatives that reinforce values and expected leadership behaviors.

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Define success metrics for programs and track participation, behavior change, and business impact.

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Collect qualitative and quantitative feedback to refine programming and improve outcomes.

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Track trends in leadership capability and recommend improvements based on data and best practices.

What we’re looking for:

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3–7+ years of experience in leadership development, organizational development, L&D, or talent management.

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Proven experience designing and facilitating leadership programs across multiple levels.

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Strong facilitation and group dynamics skills, both virtual and in-person.

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Ability to translate business goals into leadership capability frameworks and development plans.

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Experience using assessment tools (360s, psychometrics, engagement data) to guide development.

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Strong project management skills and ability to manage multiple programs simultaneously.

It’d be great if you have:

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Coaching certification or formal coaching training (ICF, Co-Active, ORSC, etc.).

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Experience with change management and organizational transformation.

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Familiarity with DEI-focused leadership development.

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Experience in high-growth, fast-paced environments.

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Knowledge of LMS/LXP platforms and modern learning technologies.

Why you’ll love it at Clutch:

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Autonomy & ownership – opportunity to build programs, tools, and influence leadership development across the company.

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Help shape the leadership culture and employee experience during a phase of rapid growth.

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Broad and direct ownership over leadership development programs and strategies.

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Exposure to senior leadership with the ability to contribute to major company initiatives.

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Competitive compensation and above-market health & dental benefits.

Employment Type:
New, Permanent Full-Time

Compensation & Benefits:

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Salary range: $100,000 - $115,000 annually

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Benefits: Comprehensive healthcare, dental, vision, prescriptions, life insurance, and dependent coverage; starting from day 1.

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Pay decisions reflect skills, performance, market benchmarking, responsibilities, and working conditions.

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 [email protected].