Chief of Staff

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Chief of Staff based in Canada.

As Chief of Staff, you will serve as a strategic operating partner to the CEO of a rapidly scaling direct-to-consumer business. You will create structure across a lean, globally distributed organization spanning e-commerce, operations, customer service, retention, and finance. The role combines executive support, operational leadership, accountability management, and hands-on execution of high-impact projects. You will build the systems, processes, and operating rhythms needed to keep teams aligned and ensure commitments translate into results. Working directly with the CEO, you will independently identify problems, remove blockers, and drive initiatives from concept through completion. This is a high-ownership environment designed for an ambitious operator who wants significant responsibility and a potential path toward senior executive leadership.

Accountabilities:

• Own accountability and urgency across functions by tracking KPIs, deadlines, commitments, and deliverables, following up with owners, removing blockers, and ensuring accountability for outcomes.
• Build and maintain a comprehensive process map of the business, including role definitions, responsibilities, recurring workflows, SOPs, documentation, reporting structures, and performance criteria.
• Triage issues and requests currently reaching the CEO by handling them directly, routing them to the appropriate owner, automating them, or eliminating unnecessary work.
• Own high-leverage projects from end to end, including growth initiatives, new channel tests, vendor negotiations, systems implementations, and other strategic projects.
• Scope projects, establish execution plans, coordinate internal and external resources, and communicate meaningful progress to the CEO without requiring step-by-step management.
• Turn conversations, meetings, Slack discussions, and other communications into clear action items with assigned owners and deadlines, then follow through until completion.
• Manage the CEO’s calendar and inbox, including scheduling, prioritization, meeting preparation, and follow-up.
• Prepare relevant materials and information to help the CEO focus time on strategic priorities such as product, partnerships, and financial performance.
• Provide direct feedback, identify performance issues early, and help managers strengthen accountability within their own teams.
• Continuously identify opportunities to improve operating standards, eliminate inefficiencies, and increase organizational effectiveness.
• Work hands-on when necessary, taking responsibility for execution rather than relying exclusively on delegation.

Requirements:

• Demonstrated ability to learn quickly and independently, with the resourcefulness to master unfamiliar tools, systems, and business domains without extensive instruction.
• Strong analytical and problem-solving abilities, with the capacity to work through complex business challenges and translate them into practical actions.
• Hands-on approach and willingness to personally execute tasks when required, regardless of seniority or perceived status of the work.
• Genuine humility, low ego, and openness to direct feedback and continuous improvement.
• Comfort operating in ambiguous environments where problems may be poorly defined and ownership is expected from the outset.
• Strong direct communication skills, with the ability to give and receive candid feedback professionally.
• High level of personal accountability, organization, prioritization, and follow-through.
• Ability to influence people and drive outcomes without relying on formal authority.
• Demonstrated capacity to operate in a demanding, fast-paced environment with a minimum expectation of approximately 50 hours per week and frequent evening or weekend work.
• Availability during U.S. Eastern Time hours within the 9:00 AM-12:00 AM ET window.
• Excellent written and spoken English.
• A proven record of excellence in a competitive academic, professional, entrepreneurial, athletic, or similarly demanding environment is preferred.
• E-commerce experience, particularly with direct-to-consumer, Amazon, or TikTok Shop businesses, is an advantage.
• Experience in subscription or customer-retention businesses is a plus.
• Previous experience as a Chief of Staff, Founder’s Associate, consultant, or investment banking professional is valued.
• Experience creating SOPs, process documentation, reporting structures, or operating cadences from scratch is preferred.
• Experience managing agencies, suppliers, or offshore contractors is an advantage.

Benefits:

• Base compensation of $6,000-$8,000 USD per month, depending on experience, with flexibility for the right candidate.
• Annual bonus equivalent to 20% of base compensation, tied to project completion and KPI achievement.
• Choice of W-2 or 1099 engagement structure.
• Fully remote work arrangement from anywhere, provided required U.S. Eastern Time availability is maintained.
• Direct exposure to senior executive decision-making and broad responsibility across the business.
• High level of autonomy and ownership over strategic and operational initiatives.
• Clearly stated potential path toward a C-suite or President-level position within two years for strong performance.
• Fast-paced, low-bureaucracy environment where results, execution, and accountability drive growth opportunities.
• Opportunity to work closely with a globally distributed team across e-commerce, operations, finance, customer service, and retention.