Chief of Staff

About Clutch:

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

Clutch is Canada’s largest buyer and seller of cars, offering a digital-first, hassle-free experience. Customers can browse thousands of cars online, have their chosen vehicle delivered right to their door, and enjoy peace of mind with our 10-Day Money-Back Guarantee.

Looking to sell? We buy over $3 million worth of cars every day, providing a firm, AI-generated offer every 15 seconds—and when you sell to us, you get paid instantly, now that’s Clutch.

Recognized four years running on The Globe & Mail’s list of Canada’s Top Growing Companies—and with back-to-back spots on Deloitte’s Technology Fast 50™ and Fast 500™—we’re seeking curious, hard-working, and driven individuals to join our growing team.

Founded in 2017 and headquartered in Toronto, Clutch currently operates in Ontario, New Brunswick, Nova Scotia, and Prince Edward Island. Our world-class investors include Altos Ventures, Canaan, FJ Labs, Brand Project, and Upper
90. To learn more, visit

Clutch is scaling quickly, and as we grow, the way we communicate, operate, and execute becomes increasingly important. We need strong systems to keep teams aligned, move priority work forward, and ensure information flows clearly across the company.

We’re looking for someone to help build and run the operating engine around the CEO and leadership team — from internal communications and company-wide meetings to executive coordination, cross-functional work streams, government relations support, and high-priority special projects.

We’re hiring a Chief of Staff to support the CEO and leadership team in driving clarity, alignment, and execution across the company.

This is a high-ownership, hands-on generalist role for someone who can operate across communications, project management, operations, administration, and cross-functional coordination. You’ll help translate company priorities into clear communications, run important operating cadences, manage company-wide meetings, support executive workflows, and drive priority work streams that do not sit neatly within one function. You’ll work closely with the CEO and partner cross-functionally with People, Finance, Legal, Operations, Product, Marketing, and other teams to help keep the company focused and moving quickly.

This is an opportunity for someone who thrives in fast-paced environments, enjoys ambiguity, and wants to work close to the center of a scaling company.

• Draft, edit, and coordinate internal communications from the CEO and leadership team, including company updates, announcements, FAQs, employee notes, and leadership messages.
• Help ensure company communications are clear, timely, practical, and aligned with Clutch’s voice and priorities.
• Build and maintain an internal communications calendar across company updates, town halls, leadership meetings, employee events, and key business milestones.
• Partner with leaders across the business to gather updates, identify important themes, and translate them into clear employee-facing communications.
• Help employees understand company priorities, performance, decisions, and changes in a clear and useful way.

• Own the planning and execution of company-wide town halls, all-hands meetings, leadership updates, and Q&A sessions.
• Build agendas, coordinate speakers, gather content, prepare slides, manage timing, and own the run-of-show.
• Work with the CEO and leadership team to shape the narrative for each company-wide meeting.
• Track employee questions, feedback, themes, and follow-up items.
• Continuously improve the quality, clarity, and usefulness of company-wide meetings.

• Plan and execute internal events such as leadership offsites, company celebrations, team-building events, onboarding moments, and employee engagement initiatives.
• Manage event logistics, including venues, catering, invites, budgets, vendors, materials, and onsite coordination.
• Partner with People, Workplace, Finance, and…