(On‑site, Mississauga – reports to the VP, Sales)

About Clutch

We're on a mission to reinvent the way people buy, sell, and own cars.

Clutch is Canada's largest online used car retailer, delivering a seamless, hassle-free car buying and selling 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, British Columbia, New Brunswick, Nova Scotia, and Prince Edward Island. Clutch is backed by a number of world-class investors, including D1 Capital, Altos Ventures, BMO Capital Partners, Canaan, Real Ventures, and others. To learn more, visit clutch.ca.

About the role

We're looking for a strategic, process-driven, and customer-obsessed leader to join our growing revenue team as Director, Sales Enablement. This role will be instrumental in equipping our sales teams with the tools, content, processes, and training they need to succeed at every stage of the buyer journey—while also leading the development of a scalable LMS platform to support 200+ employees across 6 high-impact teams.

What You'll Do

Enablement Strategy & Execution

• Develop and own the end-to-end sales enablement strategy for our Retail and Sell to Clutch teams.
• Create and execute onboarding and continuous learning programs that reduce ramp time and increase rep productivity.
• Lead the build and implementation of a Learning Management System (LMS) to support structured training for 200+ employees across Retail and Sell to Clutch teams.
• Partner with Marketing, Product, and Sales to ensure consistent, timely, and effective messaging across the customer lifecycle.
• Define and optimize key enablement processes such as content delivery, playbook creation, objection handling, and competitive intelligence.

Tools, Content & Insights

• Champion the adoption and effective use of enablement tools (e.g., Highspot, Gong, HubSpot, LMS platforms).
• Design, manage, and measure the effectiveness of sales content and training materials within the LMS and beyond.
• Drive engagement with content and surface actionable insights through usage data and feedback loops.
• Collaborate with RevOps to ensure alignment between enablement, pipeline performance, and CRM insights.

Performance Coaching & Sales Excellence

• Implement coaching programs based on call intelligence, win/loss analysis, and sales performance metrics.
• Establish KPIs to measure the impact of enablement on quota attainment, cycle time, win rate, and rep ramp.
• Work closely with sales leaders to ensure enablement initiatives are embedded in daily workflows and team rituals.

Team Leadership

• Build and lead a high-performing Sales Enablement function, growing the team as business needs evolve.
• Provide coaching, mentorship, and strategic direction to support team development and business impact.
• Foster a culture of experimentation, curiosity, and performance excellence.

What We're Looking For

• 8–10+ years in Sales Enablement, Sales Operations, or Sales Leadership, ideally in high-growth B2C or marketplace environments.
• Proven track record designing and delivering enablement programs that drive measurable improvements in sales performance.
• Experience leading the development and rollout of an LMS platform at scale to support cross-functional learning (Sales, CX, Ops, Marketing, etc.) across 200+ employees.
• Deep experience with CRM (HubSpot preferred), call intelligence (e.g., Gong), and enablement platforms.
• Strong project management and cross-functional collaboration skills; capable of navigating ambiguity and driving clarity.
• Excellent communication and facilitation skills with a knack for simplifying the complex.
• A proactive builder who balances strategic thinking with hands-on execution.
• Experience leading and scaling enablement teams, with a strong coaching mindset.

Nice to Have

• A genuine interest in Clutch's industry—automotive, marketplaces, consumer tech, or the future of retail.
• Experience operating in a Series C or Series D startup environment, where growth, ambiguity, and pace go hand-in-hand

Why Clutch

• Build the Sales Enablement function and LMS infrastructure from the ground up. You'll have the ownership and support to define what world-class enablement looks like.
• Real impact, fast: Tackle fun, complex problems in a high-growth environment where your work will influence strategy, execution, and outcomes across the company.
• Competitive package: market cash, meaningful equity, full benefits, and an in‑office culture built on transparency and pace.

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].