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, BrandProject, and Upper90. To learn more, visit clutch.ca. 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. 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. 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. What you'll 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 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. What we're looking for: • 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. 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 you'll 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: $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. • 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 talent@clutch.ca. We use AI-assisted tools to help screen and assess applications. Final hiring decisions are made by our team.