Chief of Staff

We’re Hiring: Chief of Staff | Toronto, Canada

We’re partnering with a fast-growing, AI-native legal technology company looking for a high-caliber Chief of Staff to work directly with the COO and help drive its next phase of growth.

Our client has grown 5x in just six months and is building toward becoming one of Canada’s largest consumer law businesses. This is an exciting opportunity to take ownership of high-impact strategic initiatives, improve business performance, and help shape the company’s growth trajectory.

What you’ll do:

• Partner with the COO to lead strategic and revenue-growth initiatives from concept to execution.
• Work with the sales team to improve conversion rates, optimize pricing, and identify new revenue opportunities.
• Drive operational excellence through company-wide KPIs, performance dashboards, and goal tracking.
• Own financial modeling, P&L visibility, headcount planning, and board-ready reporting.
• Conduct market research, analyze competitors, and turn insights into actionable growth strategies.

What we’re looking for:

• 4–10 years of experience across investment banking, management consulting, strategy, or startup operations.
• Experience at a high-growth technology company or startup, with a track record of building and executing initiatives.
• Strong analytical and financial modeling skills, coupled with a commercial mindset.
• Proven ability to own projects end-to-end and translate data into business outcomes.
• Excellent communication skills and the ability to work with senior leadership on confidential, high-impact decisions.

Why consider this opportunity?

• 🚀 Clear career path toward a General Manager role with full P&L ownership.
• 🎯 Direct partnership with senior leadership and ownership of business-critical initiatives.
• 📈 Opportunity to influence revenue growth, profitability, and company-wide strategy.
• 🏢 Hybrid work environment with approximately 3 days per week in the Toronto office.

Work authorization: Candidates must already be authorized to work in Canada. Visa sponsorship is not available.

Interested in building, scaling, and driving measurable business impact? Feel free to reach out or share your profile to learn more.