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.

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. Founded in 2017 and headquartered in Toronto, Clutch currently operates in Ontario, Recent Brunswick, Nova Scotia, and Prince Edward Island. 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 workstreams, 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 workstreams 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. Help employees understand company priorities, performance, decisions, and changes in a clear and useful way. Build agendas, coordinate speakers, gather content, prepare slides, manage timing, and own the run-of-show.





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.

Help create moments that build connection, culture, and alignment across the company. Drive process, workstreams, and special projects help design and implement practical process improvements. Help keep internal stakeholders aligned through explicit updates, escalation paths, and disciplined follow-through.

Support government relations and external stakeholder work Support government relations initiatives, external stakeholder engagement, and public affairs-related workstreams. Help prepare briefing materials, talking points, meeting notes, follow-ups, and stakeholder updates. Coordinate meetings, events, and logistics with external partners, government stakeholders, industry groups, and advisors.

Work with Legal, Finance, Operations, and external partners to ensure materials are accurate, polished, and well-coordinated. Track action items, deadlines, and follow-ups across government relations and external affairs projects. Support executive operations and administration Help run the operating cadence for the CEO and leadership team, including agendas, meeting notes, action items, follow-ups, and decision tracking.

Provide administrative support to the CEO and executive team where needed, including scheduling, meeting coordination, travel planning, expenses, and logistics. Help ensure key decisions are documented, owners are clear, and follow-through happens. Jump in where needed to remove friction and help the CEO and leadership team operate more effectively.

Bachelor’s degree in Business, Communications, Political Science, Public Policy, Marketing,



or a related field. ~5–10 years of experience in business operations, internal communications, executive operations, consulting, project management, government relations, public affairs, people operations, or a similar high-ownership role. ~ Strong project management skills and the ability to bring structure where none exists. ~ Strong organization and attention to detail, especially when managing multiple stakeholders, deadlines, and moving pieces. ~ Comfort working directly with senior leaders, external stakeholders, and cross-functional teams. ~ Ability to balance strategic context with hands‑on execution, including administrative and coordination‑heavy work. ~ Comfortable preparing polished slides, meeting materials, notes, briefings, and communications. ~ Strong assets Experience with government relations, public affairs, policy, or external stakeholder engagement.

Experience planning company-wide town halls, all-hands meetings, offsites, or employee events.

Experience creating executive communications, briefing materials, FAQs, board materials, or company-wide announcements.

Experience in automotive, marketplaces, fintech, consumer technology, logistics, or regulated industries. This role is based in Toronto and requires on-site presence — remote candidates will not be considered. Be part of a disruptive, tech-driven company that is transforming the automotive industry — one of the largest and fastest-growing B2C startups in Canada.

A unique opportunity to work at the center of the company, helping shape how Clutch communicates, operates, and executes as we scale. Freedom to innovate and ownership of your role — work on meaningful and challenging projects that have a direct impact on the business. Competitive pay and equity incentives.

Comprehensive health and dental perks. 160,000 - $190,000 (plus equity) Comprehensive benefits plans include healthcare, dental care, vision care, prescriptions, life insurance and dependent coverage;

Pay decisions reflect objective criteria: skills, performance, market benchmarking, responsibilities and working conditions. If you require accommodation at any stage of the interview process, please email [email protected] use AI-assisted tools to help screen and assess applications.

📌 Chief of Staff - Chief Executive Officer (Toronto)
🏢 Clutch Security
📍 Toronto