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About the Role

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.

Responsibilities

• Drive internal communications and company alignment
• 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 town halls and company-wide meetings
• 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.
• Coordinate internal events and employee moments
• 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 department leaders to ensure events are well-run and aligned with company priorities.
• Help create moments that build connection, culture, and alignment across the company.
• Drive process, workstreams, and special projects
• Own and drive cross-functional workstreams tied to company priorities, operating improvements, strategic initiatives, and executive team needs.
• Bring structure to ambiguous problems by creating clear plans, owners, timelines, and follow-up processes.
• Identify bottlenecks and gaps in how work gets done; help design and implement practical process improvements.
• Develop templates, trackers, playbooks, and lightweight operating systems that create consistency and enable scaling.
• Help keep internal stakeholders aligned through clear 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.
• Support preparation for executive meetings, leadership offsites, planning sessions, board meetings, and investor updates.
• 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.

Requirements

• 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.
• Excellent written communication skills — you can turn complex, messy, or sensitive topics into clear and thoughtful messages.
• Strong project management skills and the ability to bring structure where none exists.
• Proven ability to thrive in a high-ownership environment — you take initiative, move fast, and drive outcomes with limited oversight.
• Strong organization and attention to detail, especially when managing multiple stakeholders, deadlines, and moving pieces.
• Strong judgment and discretion when handling confidential or sensitive information.
• 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.
• Low ego, high ownership, and a willingness to roll up your sleeves.

Skills

• Experience working at a high-growth technology company.
• Experience supporting a CEO, founder, executive team, or leadership group.
• 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.
• Comfort using tools such as Google Workspace, Slack, Notion, Asana, Canva, PowerPoint, Google Slides, or similar platforms.
• Experience in automotive, marketplaces, fintech, consumer technology, logistics, or regulated industries.

Location

• Toronto

Work Type

• On-site

Experience Level

• 5-10 years

Education Level

• Bachelor's degree

Salary/Compensations

• $160,000 - $190,000 plus equity

Benefits

• Comprehensive benefits plans include healthcare, dental care, vision care, prescriptions, life insurance and dependent coverage; start from day 1.
• Competitive pay and equity incentives.
• Opportunities for growth and development in a rapidly scaling company.

About the Company

• We’re on a mission to reinvent how people buy, sell, and own cars.
• 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.
• 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, BrandProject, and Upper90.
• 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 workstreams, government relations support, and high-priority special projects.
• 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.
• Collaborate with a talented and passionate team in a dynamic, fast-paced environment.

Equal Opportunity

• 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 talent@clutch.ca.
• We use AI-assisted tools to help screen and assess applications. Final hiring decisions are made by our team.