Chief of Staff

Chief of Staff to the Founder– Founding Leadership Team

Montreal or Toronto base, Canada | $120,000–$180, 000 + Meaningful Equity

A rapidly scaling, founder led AI product company is appointing an exceptional Chief of Staff to join its founding leadership team.

Working directly with highly successful, high-profile founder, you will operate at the centre of the business—helping shape company strategy, building the organisation and driving the initiatives that will determine its next stage of growth.

This is not a traditional support position. It is a high-impact leadership role for someone with the judgement, ambition and intellectual horsepower to act as a true extension of the founders.

As one of the company’s earliest senior hires, you will receive meaningful equity and the opportunity to create substantial long-term value while helping build a category-defining AI business.

Your impact

• Partner directly with the founder on company strategy, growth and execution
• Lead the company’s most important strategic and cross-functional initiatives
• Translate ambitious goals into clear priorities, operating plans and measurable results
• Build the processes, systems and organisational infrastructure required to scale
• Drive hiring and help shape a high-performing team and company culture
• Own business performance, forecasting, financial modelling and key operating metrics
• Identify commercial opportunities and support new-market expansion
• Represent the founder across critical internal and external relationships

Your background

• 2-3 years’ experience in Top-Tier Management Consulting and
• 2-6years' experience as a Chief of Staff/Biz Ops with a founder led start up gaining experience within—or strong exposure to—a high-growth, venture-backed technology company
• An outstanding academic record from a Top University, with a Degree
• Strong commercial and financial judgement, including forecasting, financial modelling or P&L exposure
• Exceptional analytical ability and a clear bias towards action
• Genuine enthusiasm and practical use of AI, automation tools, coding or programming experience.
• The confidence and maturity to influence senior stakeholders and operate alongside founders
• A record of taking ownership and delivering results in fast-moving, ambiguous environments

Location: Montreal or Toronto, Canada – full-time, office-based

This is a rare opportunity to join at the ground floor, influence every dimension of the company and share directly in the value you help create.

If you are looking for a defining next step rather than simply another role, I would be delighted to speak with you confidentially.