Chief of Staff

About Clutch:

Were on a mission to reinvent how people buy sell and own cars. Are you game

Clutch is Canadas 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 secondsand when you sell to us you get paid instantly now thats Clutch.

Recognized four years running on The Globe & Mails list of Canadas Top Growing Companiesand with back-to-back spots on Deloittes Technology Fast 50 and Fast 500were 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. To learn more visit .

Executive Operations at Clutch

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.

Were 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.

About the role:

Were 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. Youll 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 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.

What youll do:

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 Clutchs 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.

What were looking for:

• Bachelors degree in Business Communications Political Science Public Policy Marketing or a related field.
• 510 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.

Strong assets

• 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.

This role is based in Toronto and requires on-site presence remote candidates will not be considered.

Why youll love it at Clutch:

• 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.
• Competitive pay and equity incentives.
• Comprehensive health and dental benefits.
• Opportunities for growth and development in a rapidly scaling company.

Compensation & Benefits:

• Salary range: $160000 - $190000 (plus equity)
• Benefits: Comprehensive benefits plans include healthcare dental care vision care prescriptions life insurance and dependent coverage; start from day 1.
• Pay decisions reflect objective criteria: 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 .

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