Director, Office of the CEO

Job Description

Position Summary

The Director, Office of the CEO serves as a strategic adviser and execution partner to the CEO, enhancing executive effectiveness, strengthening alignment across the leadership team, and ensuring that strategic priorities translate into measurable results. This role works closely with the CEO, COO and CAO, operating at the center of executive coordination without assuming operational ownership of functional areas.

Reports to: Chief Executive Officer

Core Purpose of the Role

• Increase the CEO’s strategic capacity
• Improve cross‑functional alignments
• Strengthen execution discipline
• 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

• Facilitate prioritization discussions across leadership
• 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

Competencies

• Structured thinker
• Politically astute
• Highly accountable
• Comfortable with ambiguity
• Bias toward action
• Able to challenge respectfully
• Resilient under pressure
• 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.