Chief of Staff to the CEO

CanadaRemoteFull-timelead

ExecutiveChief Executive Officer

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Quick Summary

Requirements Summary

12+ years of experience in operations, business operations, strategy, general management, or a Chief of Staff function, preferably within a high-growth technology environment.

Technical Tools

ExecutiveChief Executive Officer

The Chief of Staff to the CEO will play a pivotal role in connecting executive-level decisions with effective, company-wide execution. Working closely with the CEO and senior leadership team, you will help clarify priorities, anticipate organizational challenges, and ensure critical initiatives move forward with clear ownership and accountability. This strategic role requires a broad view of the business, sound judgment, and the ability to influence senior stakeholders across functions. You will strengthen leadership processes, improve communication and decision-making, and address complex issues that span organizational boundaries. The ideal candidate thrives in fast-moving technology environments, brings structure to ambiguity, and combines strategic thinking with hands-on execution. You will also help explore how AI can improve operational effectiveness and shape the way the organization works.

Translate senior leadership decisions into coordinated action by clarifying outcomes, identifying impacted teams, sequencing communications, and tracking execution.
Anticipate significant business questions, organizational constraints, and emerging risks, ensuring the appropriate leaders address them promptly.
Identify duplicated efforts, conflicting roadmaps, and cross-functional challenges without clear ownership, and facilitate resolution among accountable teams.
Own and continuously improve the senior leadership team's operating rhythm, including priority reviews, decision-making processes, and commitment tracking.
Strengthen the flow and quality of information to and from the CEO, ensuring leaders have the context needed to make informed decisions and act effectively.
Lead selected CEO-priority initiatives that do not have a natural functional owner, partnering with relevant leaders to drive them through completion.
Challenge assumptions, pressure-test leadership direction, and help ensure strategic decisions translate into consistent organizational action.

Requirements

~1 min read

12+ years of experience in operations, business operations, strategy, general management, or a Chief of Staff function, preferably within a high-growth technology environment.
Experience serving as a CEO's Chief of Staff, leading an integration or organizational transformation, or scaling operations through a significant period of growth is a strong advantage.
Demonstrated entrepreneurial ownership, such as founding a business, operating in an early-stage company, or leading an ambiguous, high-stakes initiative from definition through execution.
Proven ability to drive complex, cross-functional initiatives to completion without relying on formal authority, title, or additional headcount.
Strong executive presence, sound judgment, and a low-ego approach, with the confidence to act as an intellectual peer to senior leaders, challenge the CEO constructively, and communicate difficult messages directly.
Exceptional written and verbal communication skills, including the ability to distill complex information into concise, clear, actionable direction.
Excellent organizational skills, resilience, discretion, and follow-through, with the ability to establish structure amid ambiguity and shifting priorities.
Practical fluency in using AI tools and a well-developed perspective on how AI can transform business operations and organizational effectiveness.

What We Offer

~2 min read

✓Compensation: The original posting lists annual salary ranges for candidates based in the United States, varying by geographic market: $338,000–$413,000 for specified major metropolitan areas; $304,000–$371,000 for other specified markets; and $287,000–$351,000 for other US locations. These ranges are US-specific and do not establish a salary range for Canada.

✓Salary determination: Actual compensation in the original posting depends on factors such as job level, qualifications, skills, competencies, and proficiency.

✓Inclusive workplace: The employer emphasizes equal employment opportunities and a commitment to diversity.

✓Accessibility: Reasonable accommodations are available for candidates with disabilities during the application process.