Chief of Staff, Clutch
$160-190k
+ Equity Incentives
Canva
Slack
Asana
Notion
Google Workspace
Senior and Expert level
Toronto
5 days a week in office (Downtown Toronto, ON)
Online used car retailer
Posted today
Online used car retailer
201-500 employees
B2CMarketplaceCarsElectric VehiclesConsumer GoodseCommerce
Posted today
$160-190k
+ Equity Incentives
Canva
Slack
Asana
Notion
Google Workspace
Senior and Expert level
Toronto
5 days a week in office (Downtown Toronto, ON)
201-500 employees
B2CMarketplaceCarsElectric VehiclesConsumer GoodseCommerce
Company mission
To deliver a delightful car-buying experience to Canadians.
Role
Who you are
- 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
- 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
What the job involves
- 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
- 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
Our take
Buying used cars is notoriously something of a minefield - but used car sales platform Clutch is making big strides to sweep away the risk. The marketplace lists certified vehicles for users to shops, and has home delivery, along with a full carfax, insurance, warranty, and optional financing.
The used car sales market has been undergoing something of a digital overhaul in recent years, with a flurry of used car marketplaces cropping up to offer similar services. Canada, however, remains relatively non-competitive compared with the U.S. and Europe. This means Clutch has the luxury of importing a tried-and-tested model into a relatively spacious market.
Clutch will, however, have to face off with close competitor Canada Drives. The two companies enjoy comparable levels of funding and are currently the top competitors in Canada’s used car market. With this market hotting up significantly, Clutch will need to tread carefully to ensure they come out on top.
Steph
Company Specialist at Welcome to the Jungle
Insights
Top investors
Company
Funding (last 2 of 6 rounds)
Feb 2025
$35.6m
SERIES D
Jul 2024
$7.2m
LATE VC
Total funding: $135.2m
Company benefits
- Autonomy & ownership: Create your own path and own your work with some of the most talented and creative people in Canada
- Competitive pay + equity: Enjoy competitive pay from day one, with equity opportunities available for roles that shape our future
- Generous time off: From vacation time to parental leave, we believe that work-life harmony is key to a healthy work environment
- Health, dental & more: Your well-being matters. That's why we offer medical, dental, and wellness support to you and your loved ones
Company HQ
Downtown Yonge East, Toronto, ON
Leadership
Dan Park
(CEO)Prior to joining Clutch in 2019, Dan spent 3 years at Uber as a GM of Toronto and GM/Head of Uber Eats Canada.
Salary benchmarks
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