Chief of Staff to Executive Leadership

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Chief of Staff based in Canada.

This role offers the opportunity to work closely with executive leadership and maximize organizational effectiveness in a fast-growing SaaS environment.

You will act as a strategic partner, helping transform priorities into action while improving decision-making, communication, and operational execution.

The position combines executive support, project coordination, business operations, and strategic problem-solving.

You will help optimize leadership focus by managing critical information flows, preparing decision materials, and ensuring strong organizational follow-through.

Working across teams, you will create alignment, remove operational friction, and help accelerate high-impact initiatives.

This is an ideal opportunity for a highly organized and proactive professional who thrives in dynamic environments and enjoys creating clarity from complexity.

You will play a key role in increasing executive leverage and enabling the organization to achieve its most important goals.

Accountabilities

Responsibilities

The Chief of Staff will support executive leadership by improving operational efficiency, managing priorities, and ensuring important initiatives move forward effectively. Key responsibilities include:

• Partner closely with executive leadership to manage priorities, improve decision-making, and maximize time spent on high-impact activities.
• Attend key meetings, capture decisions, document action items, assign owners, and ensure commitments are completed.
• Maintain centralized tracking systems for leadership priorities, cross-functional projects, and organizational follow-ups.
• Coordinate with teams to ensure important information, insights, and decisions from customers, partners, investors, and employees reach the appropriate stakeholders.
• Support leadership meetings by preparing agendas, identifying required decisions, gathering missing information, and driving follow-through.
• Create executive briefs, meeting preparation materials, reports, and summaries for strategic discussions, board meetings, business reviews, and leadership sessions.
• Transform complex information, discussions, and documents into clear insights, recommendations, and actionable next steps.
• Bring strategic perspective to decision-making by identifying risks, opportunities, and potential solutions.
• Manage and optimize executive calendars by prioritizing meetings, protecting focus time, and ensuring efficient scheduling.
• Coordinate travel, events, meetings, and logistics while anticipating potential challenges before they arise.
• Support communication management by organizing inboxes, prioritizing requests, handling appropriate follow-ups, and reducing unnecessary executive workload.

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• Act as a trusted representative when appropriate by managing communications and ensuring alignment across stakeholders.
• Provide personal administrative support when needed while maintaining professionalism and discretion.
• Help establish organizational frameworks, reporting processes, goal-setting systems, and operational rhythms.
• Drive accountability across teams by ensuring commitments are tracked, communicated, and successfully completed.
  
  

Requirements

The ideal candidate is a highly organized, proactive, and resourceful operator with strong judgment, communication skills, and experience supporting senior executives in dynamic environments. Required qualifications include:

• 5+ years of experience supporting a CEO, founder, executive leader, or senior leadership team.
• Experience working in a fast-growing, entrepreneurial, or high-performance environment.
• Strong executive calendar, inbox, travel, meeting management, and administrative support skills.
• Excellent written and verbal communication abilities with strong attention to detail.
• Proven ability to manage multiple priorities, projects, and stakeholders simultaneously.
• Strong project management skills with exceptional follow-through and accountability.
• Ability to anticipate needs, identify risks, and solve problems before they become obstacles.
• Comfortable holding senior leaders and teams accountable while maintaining strong relationships.
• High level of discretion and maturity when handling confidential business and personal information.
• Ability to transform ambiguity and complex situations into structured plans and clear actions.
• Strong judgment and ability to independently determine priorities and information flow.
• Service-oriented mindset combined with the confidence to provide recommendations and challenge assumptions when needed.
• Comfortable using modern business tools, including AI platforms, Google Workspace, Slack, project management systems, and productivity tools.

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• Experience working with executives, boards, investors, or external professional partners is an advantage.
  
  

Benefits

• Competitive salary package with equity opportunities.
• Fully remote work environment with flexibility and trust.
• Comprehensive employee benefits supporting wellbeing and work-life balance.
• Paid vacation time and additional life leave days.
• Opportunity to work closely with executive leadership and influence company-wide priorities.
• Career growth opportunities within a fast-growing technology organization.
• Collaborative culture focused on innovation, customers, product excellence, and growth.
• Team lunches, off-sites, and opportunities to build strong relationships with colleagues.
• Inclusive workplace committed to diversity, accessibility, and creating an environment where everyone can thrive.
• Opportunity to contribute to a meaningful mission focused on empowering creativity through technology.
  
  

How Jobgether Works

We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team.

We appreciate your interest and wish you the best!

Why Apply Through Jobgether?

Data Privacy Notice: By submitting your application, you acknowledge that Jobgether will process your personal data to evaluate your candidacy and share relevant information with the hiring employer. This processing is based on legitimate interest and pre-contractual measures under applicable data protection laws (including GDPR). You may exercise your rights (access, rectification, erasure, objection) at any time.

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.