Chief of Staff

Chief of Staff - Markham, ON

Compensation: $130,000 - $160,000 + bonus component

Role Overview

The Chief of Staff, CEO Office is a trusted strategic advisor and operational partner to the CEO, enabling the CEO to focus on the highest-value priorities that drive the continued growth and long-term success. Acting as an extension of the CEO, the Chief of Staff translates strategic priorities into action, ensures strong execution across key initiatives, and supports alignment among the senior leadership team.

This role spans strategy, operations, communications, governance, stakeholder management, and employee engagement. The Chief of Staff works closely with the CEO, senior leaders, parent-company stakeholders, and external partners to advance enterprise priorities and ensure disciplined follow-through on critical business matters.

The ideal candidate is a highly analytical and structured problem-solver with exceptional communication, interpersonal, and organizational skills. They bring strong business judgment, executive presence, discretion, and a high degree of ownership. They are comfortable operating in ambiguity, managing multiple priorities, and moving seamlessly between strategic and tactical work. The Chief of Staff also leads a team of three across strategy, communications, events, and engagement.

Key Responsibilities

CEO Support and Executive Effectiveness

• Manage and triage the CEO’s workflow, ensuring the CEO’s time and attention are focused on the highest-priority matters.
• Assess inquiries, requests, and issues directed to the CEO; determine the appropriate course of action, delegate where appropriate, and ensure timely follow-up.
• Prepare the CEO for internal and external meetings through briefing notes, pre-read materials, talking points, and decision-support materials.
• Accompany the CEO to critical meetings or act as a proxy or representative at meetings, events, and functions as needed.
• Serve as strategic thought partner on AI, identifying emerging trends, evaluating opportunities, and advising on how AI can accelerate business performance and innovation. Lead AI initiatives as required.
• Lead strategic initiatives and special projects as directed by the CEO, ensuring clear objectives, disciplined execution, and measurable outcomes.
• Serve as a strategic thought partner, sounding board, and confidante to the CEO.

CEO Communications and External Stakeholder Relations

• Draft CEO communications, including presentations, press release quotes, interview talking points, speeches, executive correspondence, and internal messages.
• Capture and maintain the CEO’s authentic voice across internal, external, and board-level communications.
• Coordinate speaking engagements for the CEO and develop supporting materials as required.
• Foster and strengthen key relationships across government, industry, academia, community partners, and other external stakeholders on behalf of the CEO.
• Support external copywriting as needed, including private label product descriptions, product naming, in-store signage, and customer communications.

Leadership Effectiveness, Operating Rhythm, and Strategic Planning

• Create cohesion and alignment among the leadership team by owning agendas, materials, and follow-through for weekly and monthly leadership meetings.
• Drive the company’s operating rhythm, including quarterly business reviews, KPI tracking, initiative tracking, and leadership follow-ups.
• Promote leadership team effectiveness by improving collaboration, communication, accountability, and decision-making.
• Surface opportunities and gaps across people, structure, culture, and operating processes; partner with the CEO and leadership team to develop practical solutions.
• Lead annual corporate planning activities, including strategic planning cycles, leadership retreats, agenda-setting, materials development, and follow-through.

Board and Parent-Company Communications

• Manage board meeting preparation, including agenda development, presentation materials, briefing documents, and coordination with the CEO and business leaders.
• Support the development of enterprise-level strategic narratives, business updates, and executive presentations.
• Serve as the primary coordination point between the CEO Office and Loblaw parent-company stakeholders on cross-enterprise initiatives, reporting requirements, and strategic planning cycles.
• Ensure strategic priorities are translated into clear workplans, governance structures, milestones, and accountability mechanisms.

Internal Communications, Employee Engagement, and Community Impact

• Develop employee communication strategies and materials to support organizational change, culture-building, and company-wide alignment.
• Draft the CEO’s internal newsletter and other CEO-led communications to reinforce culture, priorities, and business direction.
• Organize town halls, CEO-led speaking engagements, weekly company-wide huddles, employee engagement events, staff appreciation programs, and new store opening activities.
• Provide oversight and management of the charitable foundation and community impact initiatives, including governance, operations, partner engagement, and events.
• Partner with the CEO to shape the foundation’s mission, vision, priorities, and operating model.

Qualifications and Requirements

• 10+ years of progressive professional experience in one or more of the following areas: Chief of Staff, enterprise or corporate strategy, management consulting, corporate development, business transformation, executive office, or senior operating roles within a complex organization.
• Bachelor’s degree required; degree in business, strategy, communications, or a related field preferred.
• Retail, grocery, consumer goods, or multi-unit operating experience considered a strong asset.
• Bilingual English/Mandarin or English/Cantonese considered a strong asset.
• Demonstrate AI fluency and strategic thinking; experience leading AI-enabled transformation an asset.
• Strong strategic foresight, business judgment, and financial acumen, with the ability to connect dots across a large, matrixed business and anticipate the needs of the CEO and leadership team.
• Exceptional written and verbal communication skills, including the ability to write in an executive’s voice and adapt tone for internal, external, board-level, and employee-facing audiences.
• Proven people leadership experience, with the ability to manage, coach, and develop a high-performing team.
• Highly analytical and structured problem-solver, with strong project and program management skills and the ability to drive multiple priorities under tight deadlines.
• Strong relationship-building and influencing skills, with the ability to earn trust quickly and work effectively across all levels of the organization, including senior leaders, board members, parent-company stakeholders, and external partners.
• Cross-functional operating capability across areas such as finance, operations, merchandising, marketing, HR, technology, supply chain, and store operations.
• Adaptable, resilient, and comfortable operating in ambiguity while moving between strategic and tactical work.
• High level of integrity, judgment, and discretion in handling sensitive and confidential information.