Senior Director, Strategic Initiatives

Job Type:Permanent
** Department:
** Executive Services
** Salary:**$ - $
** Close Date** ***(closes at 12:00 am on date noted below):
*** January 4, 2026
** Hours per Week:
** 35

Openings:1# #
** Position Summary
** The Town of Milton is one of Ontario’s fastest-growing communities, strategically located in the Greater Toronto Area. Known as “A Place of Possibility” we are laying the groundwork for our vision Milton 2051, with a strong commitment to creating complete, connected communities, fostering innovation and opportunities to live, learn, work, and play.  Reporting to the Chief Administrative Officer (CAO) the Senior Director, Strategic Initiatives is a trusted advisor, supporting the CAO and the Senior Leadership Team (SMT) in advancing the Town’s strategic priorities.

This position leads the development and implementation of strategies and initiatives, oversees the Town’s Economic Development team and is responsible for building and leading the Town’s government relations program.
The Senior Director, Strategic Initiatives is also responsible for fostering a culture of innovation, championing creative problem solving, leading change, and leveraging technology, data, and collaborative partnerships to modernize service delivery.# #
** Major

Job Responsibilities
*** Proactively identifies corporate issues and challenges, analyzing impacts and recommending solutions that align with organizational priorities.
* Champions innovation across the organization by introducing new ideas, processes, and solutions, and by identifying emerging trends and opportunities to enhance service delivery.
* Leads the development and implementation of strategic plans that align municipal priorities with long-term goals
* Acts as a trusted advisor to the CAO and senior leaders in decision making and implementing strategic initiatives.
* Provides support to the CAO through briefings and related materials.
* Represents the Office of the CAO, observing and participating in committees, task forces, community forums, fostering positive working relationships within and outside the organization, and identifying new opportunities for partnership or collective action on common objectives/initiatives.
* Follows up and reports on progress of Council directives, strategic initiatives and projects, ensuring they are effectively moving forward and identifying opportunities to improve the effectiveness of such, as required.
* Responds to Council inquiries/concerns and manages competing interests and priorities with a high degree of political acuity.
* Facilitates and coordinates the corporate business planning process, and monitors key activities, department performance and reporting.
* Analyzes and recommends business strategies, potential actions and alternative solutions to the CAO and the SMT.
* Measures performance using associated KPIs to maximize effectiveness in delivering business and project outcomes in alignment with the overall corporate priorities.
* Leads the development and implementation of data-driven frameworks to assess the impact and success of strategic initiatives.
* Promotes individual, team and corporate accountability through leadership and coaching in the advancement of corporate priorities with a focus on maximizing organizational performance and continuous improvement.
* Assists leadership teams and acts as a change agent in developing different perspectives and possibilities, and challenges ideas to foster an environment of innovation, accountability and continuous improvement.
* Maintains effective working relationships with internal and external stakeholders, including other levels of government, agencies and community partners.
* Develops and leads the government relations program, including managing external consultant agencies
* Provides leadership and direction to the Economic Development team#
** Education & Experience
*** Post-secondary degree
* Ten (10) years of progressive municipal experience, including experience working directly with and providing strategic advice and input to senior-level staff, politicians and other levels of government
* · Proven experience successfully leading innovation and the process…