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
Compensation: $120,000–$180,000 plus meaningful equity
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.
