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.
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Chief of Staff to Founder in Montréal employer: Wintermeyer Ventures
As an Agent Deployment Engineer at our company, you'll be part of a dynamic and innovative team in Toronto, where collaboration and technical excellence are at the forefront of our work culture. We offer competitive compensation, opportunities for professional growth, and a chance to make a significant impact by delivering cutting-edge AI solutions to enterprise customers. Join us to thrive in a fast-paced environment that values your contributions and fosters continuous learning.
