Chief of Staff to CEO

Responsibilities

- Executive & Strategic Support: Serve as a trusted strategic partner to the CEO and Group Editor, providing high-level support in strategic planning, decision-making, business priorities, and execution of key initiatives.
- Executive Office Management: Act as an extension of the CEO and Group Editor, helping manage priorities, coordinate key activities, anticipate needs, and ensure that strategic and operational objectives are followed through effectively.
- Calendar & Priority Management: Manage and coordinate complex executive calendars, meetings, travel, and commitments, ensuring that the CEO and Group Editor remain focused on the organization’s highest-priority objectives.
- Communication Management: Serve as a key point of contact for internal and external stakeholders. Screen, prioritize, and coordinate communications, ensuring important matters are escalated appropriately and information flows efficiently across the organization.
- Meeting & Leadership Coordination: Organize and coordinate executive meetings, leadership meetings, conferences, and strategic sessions. Prepare agendas and briefing materials, document key decisions, track action items, and ensure timely follow-up and accountability.
- Project & Initiative Management: Lead and coordinate strategic projects, special initiatives, and cross-functional priorities on behalf of the CEO and Group Editor. Establish timelines, coordinate stakeholders, monitor progress, identify risks, and provide regular updates to senior management.
- Cross-Functional Leadership: Work closely with department heads, senior executives, and key team members to align priorities, facilitate collaboration, remove obstacles, and ensure that organizational initiatives are executed effectively.
- Executive Decision Support: Conduct research, analyze information, prepare reports and presentations, and provide insights to support executive decision-making. Identify trends, opportunities, risks, and potential solutions relevant to the organization.
- Research & Analysis: Conduct research on industry trends, competitors, market developments, business opportunities, and strategic issues. Translate findings into concise insights and recommendations for the CEO and Group Editor.
- Board & Senior Stakeholder Support: Assist with preparation for board meetings, executive leadership meetings, investor or partner meetings, and other high-level engagements. Prepare briefing materials, presentations, agendas, and follow-up documentation as required.




- Document & Presentation Preparation: Draft, proofread, edit, and coordinate executive correspondence, presentations, reports, briefing documents, proposals, and other materials requiring a high level of accuracy and professionalism.
- Information & Confidentiality Management: Manage confidential and sensitive information, files, records, and executive documentation with a high degree of discretion, judgment, and professionalism.
- Relationship Management: Build and maintain strong relationships with senior executives, employees, clients, partners, stakeholders, and external contacts on behalf of the CEO and Group Editor.
- Operational Support: Partner with leadership and administrative teams to identify operational needs, improve processes, resolve issues, and support the effective functioning of the executive office.
- Office & Administrative Oversight: Maintain oversight of key administrative requirements, office operations, executive resources, supplies, equipment, and other activities necessary to support an efficient executive office.
- Follow-Through & Accountability: Maintain visibility into organizational priorities and commitments, follow up with relevant stakeholders, track deadlines, and ensure that decisions and initiatives move from discussion to execution.
- Special Projects: Take ownership of high-priority, confidential, or time-sensitive projects assigned by the CEO or Group Editor, often working independently and across multiple departments.

Qualifications

- Education: Bachelor’s degree in business administration, communications, management, or a related field. Additional qualifications in leadership, project management, business strategy, or executive management are an asset.
- Experience: Proven experience in a Chief of Staff, Executive Assistant, Business Operations, Project Management, Strategy, or senior administrative role supporting C-suite executives or senior leadership.
- Strategic Thinking: Strong ability to understand the broader business context, identify priorities, anticipate challenges, connect information across departments, and support strategic decision-making.
- Organizational & Project Management Skills:



Exceptional organizational and multitasking abilities, with demonstrated experience managing multiple priorities, complex projects, deadlines, and stakeholders simultaneously.
- Communication Skills: Excellent written and verbal communication skills, with the ability to communicate effectively and professionally with employees, executives, clients, partners, and other senior stakeholders.
- Leadership & Influence: Ability to lead initiatives, coordinate cross-functional teams, influence stakeholders, and drive accountability without necessarily having direct authority over team members.
- Executive Presence: Professional, confident, mature, and capable of representing the CEO and Group Editor with discretion and credibility in internal and external interactions.
- Problem-Solving & Judgment: Strong analytical and problem-solving skills, with the ability to anticipate issues, evaluate options, make sound recommendations, and handle sensitive situations with good judgment.
- Attention to Detail: Exceptional attention to detail in scheduling, communications, presentations, reports, meeting preparation, project tracking, and information management.
- Discretion & Confidentiality: Demonstrated ability to manage highly confidential business, executive, personnel, and strategic information with integrity and discretion.
- Adaptability: Comfortable working in a fast-paced, agile environment where priorities can change quickly. Able to remain calm, flexible, and solutions-oriented under pressure.
- Technology Proficiency: Strong proficiency in Microsoft Office Suite, including Word, Excel, PowerPoint, and Outlook, as well as calendar management, collaboration, project management, and other business productivity tools.
- Professionalism & Initiative: Highly proactive, resourceful, and self-directed, with the ability to anticipate the needs of senior leadership, take ownership of responsibilities, and operate with a high degree of independence.

Key Competencies

- Strategic thinking and execution
- Executive leadership support
- Project and program management
- Cross-functional coordination
- Stakeholder and relationship management
- Business research and analysis
- Communication and executive correspondence
- Decision support
- Prioritization and time management
- Confidentiality and discretion
- Problem-solving and sound judgment
- Leadership without direct authority
- High attention to detail
- Proactive and solutions-oriented approach

📌 Chief of Staff to CEO & Group Editor (Mississauga)
🏢 Y MEDIA GROUP
📍 Mississauga