Director, Office CEO

Position: Director, Office of the CEO
The Director, Office of the CEO serves as a strategic advisor and execution partner to the CEO.

This role exists to enhance executive effectiveness, strengthen alignment across the leadership team, and ensure that strategic priorities translate into measurable results.

Working in close partnership with the CEO and alongside the COO and CAO, this position operates at the center of executive coordination without assuming operational ownership of functional areas.

Core Purpose of the Role

Increase the CEO’s strategic capacity

Improve cross-functional alignments

Surface risk and opportunity early

Drive clarity and accountability at the executive level

Key Responsibilities
Strategic Planning & CEO Advisory

Partner with the CEO in annual and quarterly planning processes

Support development and tracking of corporate objectives and priorities

Translate strategic discussions into structured action plans

Conduct analysis to inform executive decision making

Prepare board materials and executive level presentations

Executive Alignment & Governance Support

Attend executive leadership and cross-functional meetings

Capture decisions, risks, and accountability owners

Monitor progress on strategic initiatives

Identify execution gaps or misalignment across departments

Ensure leadership cadence and review rhythms are maintained

Business Performance & Insight

Develop executive dashboards and summary reporting

Analyze financial and operational data to support CEO decisions

Evaluate business cases for major initiatives

Provide structured insight into growth risks and performance trends

Cross-Functional Strategic Initiatives

Lead or coordinate CEO-sponsored initiatives

Facilitate collaboration across departments on priority projects

Remove barriers impacting execution of strategic goals

Support high-impact corporate initiatives as required

CEO Office Management

Manage CEO calendar aligned to strategic priorities

Filter and synthesize incoming information

Prepare briefing materials in advance of key engagements

Draft executive communications as required

Represent the CEO in designated internal forums

Decision Authority

Drive execution of CEO-sponsored initiatives

Represent the CEO in internal meetings when delegated

Make recommendations regarding strategic trade-offs

Final authority remains with the CEO and respective functional executives.

Qualifications

7–12 years of experience in strategy, consulting, operations, or executive advisory roles

Experience supporting senior leadership in growth environments

Strong financial and business acumen

Advanced analytical and problem-solving capability

Exceptional written and verbal communication skills

Executive maturity, discretion, and sound judgment

Ability to influence without formal authority

Preferred

MBA or equivalent strategic training

Experience preparing board-level materials

Structured thinker

Politically astute

Highly accountable

Comfortable with ambiguity

Bias toward action

Able to challenge respectfully

Excellent communication skills both written and verbal

What's in it for you? (Salary, Commissions & Benefits)

On-site position located in Brampton, ON, Canada — join a collaborative team in our local office

Competitive base salary as the core of your compensation package

Full Health and Dental Benefits

Pillway is an inclusive employer and provides accommodations for applicants with disabilities throughout the recruitment process. Please let us know if you require accommodation.

Pillway uses Workwolf’s AI-enabled tools to sort and screen applications based on job-related criteria. All hiring decisions involve human review.

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