Chief of Staff to Founder
$10k per yearWintermeyer Ventures
About the Role
A Canadian textile manufacturing business is seeking a Chief of Staff to turn founder priorities into completed, measurable projects. This hands-on role works across growth, operations, finance, recruiting, suppliers, and technology to help the business execute effectively.
What You'll Do
- Translate ambiguous priorities into clear plans, owners, deadlines, decisions, and measurable outcomes.
- Lead cross-functional projects involving product costing, sourcing, operational improvements, financial analysis, and recruiting.
- Coordinate urgent issues, follow up with stakeholders, and independently close action items.
- Prepare concise briefs, financial models, dashboards, and action records to support decisions.
- Coordinate with technical specialists and vendors on projects involving software, data, or automation.
What We're Looking For
- One to ten years of experience as a chief of staff, founder, or operator, including experience executing ambiguous, multi-team projects.
- Advanced spreadsheet skills, including quantitative analysis, unit economics, and financial modeling; experience with Google Workspace and Google Sheets is relevant.
- Strong written communication, prioritization, discretion, stakeholder management, and hands-on execution skills.
- Experience beyond account executive or sales engineering roles, ideally including a startup and founder-office or operating environment.
- Technical background or practical fluency with AI, software, or data is a plus; coding is not required. Experience using AI tools and checking their outputs is also valuable.
- Canadian work authorization and willingness to work in person five days per week in Montréal, or relocate within Canada.
Compensation & Benefits
Base salary: $70,530 to $105,796 USD annually. Visa sponsorship is not available. For hires relocating to work in person in Montréal or Saint-Jean-sur-Richelieu, reimbursement of up to C$10,000 is available for pre-approved, receipt-backed moving and short-term accommodation expenses.
Location
On-site, five days per week in Montréal, Quebec, Canada. Saint-Jean-sur-Richelieu is also a possible work location.
Vacancy posted 2 days ago
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