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

- Robust 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 quick, 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

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

📌 Chief of Staff (Toronto)
🏢 Clutch
📍 Toronto