The Town of Caledon is a dynamic municipality that successfully balances urban, rural and agricultural communities. Our energetic staff are guided by our core values that create an environment for continuous improvement and customer service excellence.

In addition to offering exciting career opportunities, the Town also provides a competitive and comprehensive total rewards package. Come see how you can make a difference*.*

The Opportunity

Reporting directly to the Chief Administrative Officer (CAO), the Director, Office of the CAO / Chief Strategy Officer is responsible for shaping long-term strategic planning that aligns with Caledon’s Strategic Priorities and community expectations. The ideal candidate is a dynamic, visionary leader with extensive experience in government relations, public policy, strategic planning, and pioneering complex/transformational change in public sector service delivery.

As a primary advisor to the CAO, the Director ensures the alignment of all activities within the CAO’s office to the Caledon Strategic Plan and champions innovation across the organization. This role is responsible for enhancing the effectiveness of the CAO’s Office by leading a multi-disciplinary team of specialists across strategic initiatives, internal audit, government relations and public affairs. The Director fosters strong working relationships with the team while ensuring ownership, accountability to drive progress and a commitment to the Town’s core values.

As the Director, Office of the CAO/Chief Strategy Officer you will perform the following duties, including but not limited to:

Functional Responsibilities:

• Provide strategic leadership and counsel to the CAO across a politically sensitive, multi-stakeholder landscape. Act as a trusted advisor on both strategy and practical execution, liaising between different functional areas and ensuring that the organization is agile enough to quickly adapt to changes.
• Ensure that the organization has a consistent view of Caledon’s Strategic Priorities, and facilitate strategically sound decision-making by aligning corporate, departmental, and cross-departmental objectives.
• Influence the perspective of senior leadership to challenge entrenched views on traditional municipal service delivery. Assess the appetite and ambition for change with the organization, as well the priorities of departmental leadership to drive results on discretionary strategic programs; act as a change facilitator when leading these initiatives.
• Own the organizational performance measurement process. Link the Strategic Plan into actionable outcomes and ensure all departments across the organization are equipped with the tools to plan, implement, and track relevant strategic initiatives and performance against defined metrics.
• Lead the team through procedural and organizational change to ensure they can handle evolving demands. Motivate staff to commit to organizational vision to ensure maximized participation in change efforts.
• Work with staff from across the Town to build strong, collaborative relationships, and advise the implementation of cross-corporate projects, strategic planning, and policies and procedures to meet the various service requirements.
• Oversee the preparation of the annual operating and capital budget for the Office of the CAO, work with other divisions to ensure overall budgets are coordinated and aligned with corporate direction.

The Ideal Candidate

We are seeking an experienced professional with a post-secondary degree in Information Technology, Business Management, Public Administration, Public Policy, Political Science, Economics, or a closely related field. A master’s degree in public administration, Public Policy, Political Science, Economics, or a closely related field is an asset. Our ideal candidate has a minimum of eight (8) years’ experience in management consulting, continuous improvement, and/or transformation and a minimum of five (5) years of people leadership experience in a senior management role (Chief Strategy Officer preferred).

Certifications in Project Management, Change Management (Practitioner/Professional) and/or Lean Greenbelt Certification preferred.

The ideal candidate will have experience in a policy development and/ or project management role within a government setting, or large-scale organizational change efforts; municipal experience and familiarity with regulatory requirements is considered an asset. We are seeking an individual with strong analytical acumen, adept at simplifying complex problems, and skilled in orchestrating effective plans to address challenges and minimize risks.

The successful candidate for Director, Office of the CAO/Chief Strategy Officer will be required to work a flexible schedule, including in the office, remotely and after hours (as required).

This position offers a salary range of $173,198.69 to $216,498.36 plus a competitive benefit package.

Satisfactory passing of a criminal record check, and proof of qualifications will be required of any successful candidate(s) for this position.

The Town is committed to diversity and inclusivity in employment and welcomes applications from qualified individuals of diverse backgrounds. The Town is an equal opportunity employer that is committed to an inclusive and barrier-free workplace. If your application requires accommodation, please contact People Services at (905) 584-2272 Ext. 4738.

Applications for this posting will be accepted until August 15th***, 2025, 12:00PM EST****.*