Chief Administrative Officer

Winnipeg, the 'heart of the continent,' is Canada's 7th largest city, with a population of 843,640 (2024) and steadily climbing. Located within Treaty No. 1 Territory, the traditional lands of the Anishinabe (Ojibway), Ininew (Cree), Oji-Cree, Dene, and Dakota, and the Birthplace of the Métis Nation, Winnipeg is a dynamic and diverse urban hub with the largest population of Indigenous peoples out of all major Canadian cities. We are celebrated for our vibrant arts and cultural scene and proximity to breathtaking lakes and natural environments – it is a playground for all seasons.

Winnipeg also boasts one of Canada's most diversified economies, featuring robust trade, technology, manufacturing, and agri-business sectors. It is home to thriving financial and insurance services, leading educational and healthcare institutions, and growing industries such as television, film, video game production, and aerospace.

The City of Winnipeg is seeking it's next Chief Administrative Officer (CAO) to lead this expanding community into the next chapter with innovative strategies focusing on transformative change, customer service excellence and forward-thinking solutions . Reporting directly to the Mayor, Executive Policy Committee, and Council, the CAO will provide strategic direction, oversee the City's operations, and ensure Winnipeg's public service delivers exceptional service to residents while adapting to the needs of a rapidly growing and thriving metropolitan city.

The CAO will be a catalyst for progress, bringing a proven track record of leading large, complex, and unionized organizations, driving transformation within diverse business streams and multifaceted operations. With a workforce of over 10,000 unionized employees across 23 business units and 8 major departments, the CAO will have experience in labor relations, collective bargaining, and workforce engagement. The role requires a leader experienced in fostering a collaborative culture focused on innovation, responsiveness, and continuous improvement, while empowering employees to deliver efficient, high-quality services and challenge the status quo.

Working with the Mayor, Council, and key stakeholders, the CAO will align municipal operations with strategic priorities , balancing fiscal responsibility with operational excellence. This includes developing innovative approaches and technologies to streamline processes and assessing and building high-performing leadership teams to champion meaningful change.

The successful candidate will also oversee a multi-billion-dollar operating and capital budget and lead initiatives to address systemic inefficiencies, standardize operations, and foster accountability across all levels of the organization. Through effective resource management and an accountable leadership philosophy, the CAO will ensure Winnipeg's public service operates with transparency, integrity, and a commitment to meeting the needs of a dynamic, growing community.

Key Responsibilities:

Strategic Planning and Organizational Leadership

• Serve as a catalyst for structural and process enhancements, breaking down organizational silos to foster a unified and efficient public service.
• Develop, coordinate and implement strategic, multi-year development plans that align with the City's mission, vision, and long-term goals.
• Collaborate with City departments to ensure alignment with Council and Mayor's priorities while fostering partnerships with provincial, federal, and Indigenous governments, as well as key industry stakeholders.

Core Operations and Service Delivery

• Lead and manage the City's operational services, ensuring high-quality customer service for all citizens.
• Establish and maintain efficient systems and processes, promoting continuous improvement methodologies for delivering services effectively and efficiently.
• Oversee significant city projects and assets, ensuring accountability and sustainable practices.
• Direct the Emergency Operations Centre during crises, collaborating with the Mayor's Office to declare states of emergency when necessary.

Financial Management and Accountability

• Partner with the CFO to develop and oversee a multi-billion-dollar annual operating and capital budget, ensuring fiscal responsibility and alignment with strategic priorities.
• Approve and allocate resources, monitor variances, and address significant budgetary challenges while ensuring long-term financial sustainability and optimization of taxpayer dollars.
• Provide transparency and accountability in financial reporting to Council and citizens.

Workforce Leadership and Engagement

• Directly manage senior leadership, including department directors, and oversee a workforce of over 10,000 unionized employees.
• Address labour matters, including collective bargaining for eight unions, fostering collaboration in a unionized environment.
• Champion a corporate culture of service excellence, cultivating staff morale while uniting the organization's diverse workforce and fostering inclusivity, equity, and respect.

Stakeholder Engagement

• Build and maintain respectful relationships with governments, businesses, community leaders, and citizens.
• Actively participate in public forums, media engagements, and intergovernmental initiatives.
• Ensure the City's services are accessible and reflective of community needs, fostering transparency and public trust.

Ideal Qualifications and Experience:

• Leadership : A proven track record of executive-level leadership in large, complex, multi-department organizations with demonstrated experience delivering a culture of customer service excellence and building high-performing teams to execute organizational goals.
• Organizational Transformation: Demonstrated expertise in leading restructuring efforts, optimizing workforce strategies, and driving cultural change initiatives to enhance operational efficiency and align human capital with organizational goals.
• Financial Acumen: Extensive experience in managing large-scale budgets to ensure fiscal accountability and support strategic initiatives within a complex municipal structure.
• Stakeholder and Community Relations : Skilled in building and maintaining strong relationships with key stakeholders, community partners, and industry leaders to foster collaboration, enhance organizational reputation, and achieve shared goals.
• Education : A post-secondary degree in public administration, business, economics, political science, policy, or a related discipline. A Masters or advanced degree is preferred.

Experience :

A minimum of 15 years of management experience, including 5 years in executive roles and 7-10 years leading similar large-scale services.

Expertise in strategic planning, organizational transformation, and process improvement.

Experience leading in a unionized environment.

• Skills : Exceptional communication, political acumen, financial management, and relationship-building skills. Ability to drive change and foster collaboration across diverse teams and stakeholders.
• Knowledge : In-depth understanding of municipal operations, public policy, governance, and risk management.

Discover more about this opportunity and Winnipeg here:

Submitting Your Candidacy:

The City of Winnipeg is committed to equity, diversity, and inclusion, aiming to reflect the community it serves. Please submit your cover letter and resume to Annette Kohut, Senior Associate, Executive Search, at akohut@peoplefirsthr.com.

For further information or questions, contact Karin Pooley, Vice-President, Executive Search, at 204-940-3939.

The deadline for applications is March 10, 2025.