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Chief of StaffConfidential • Toronto, Ontario, CA
Chief of Staff

Chief of Staff

Confidential • Toronto, Ontario, CA
12 days ago
Job type
  • Full-time
Job description
Chief of Staff About the Company Innovative proprietary technology platform serving retail companies Industry Internet Type Privately Held, VC-backed Founded 2016 Employees 1001-5000 Categories - Analytics Finance Retail - Internet - Technology - Venture Capital - Specialties - venture capital and financial technology - venture capital - financial technology - digital transformation - e-commerce - and retail - retail - artificial intelligence - ai - machine learning - private equity - m&a - and mergers Business Classifications - B2C - B2B About the Role The Company is seeking a Chief of Staff to the CEO and CTO. This pivotal role is not for the faint of heart; it demands a seasoned professional with a minimum of 7 years' experience in strategy and operations, a founder's/executive office, consulting, banking, finance, product operations, or technical program leadership. The successful candidate will be responsible for turning high-velocity discussions into durable decisions, clear ownership, and completed work, effectively building the connective system between company strategy, technology strategy, and day-to-day execution. This is a hands-on position that requires the ability to challenge weak reasoning, spot unresolved issues, and drive work to a measurable outcome. The Chief of Staff will also be instrumental in running the executive decision system, maintaining the executive cadence, and ensuring that priority initiatives are executed with precision. Applicants for the Chief of Staff role at the company should possess exceptional written and verbal communication skills, strong business and financial fluency, and enough technical fluency to work credibly with engineering, data, AI, and security leaders. The role demands a professional with a proven track record of driving cross-functional initiatives, excellent judgment, and the ability to operate with high discretion and low ego. Strategic thinking, the ability to work at high velocity, and a comfort with operating across time zones are essential. The Chief of Staff will also be expected to have a strong background in metrics, economics, and experimental rigor, and to partner with various teams to turn ambiguous questions into testable hypotheses. The position is ideal for a builder who takes ownership, moves fast, and is eager to see the direct impact of their work. Hiring Manager Title Chief Executive Officer Functions - General Management - Strategy - Operations
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Chief of Staff • Toronto, Ontario, CA

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