Senior Director, Strategic Initiatives

Job Type:

Permanent

Department:

Executive Services

Salary:

$178,588.00 - $223,235.00

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 of creating, implementing, monitoring and evaluating corporate strategic plans and initiatives with proven results

• Experience working closely with economic development, the business community or community partners is an asset

• Demonstrated experience in developing and utilizing performance metrics, dashboards, and reporting tools to support strategic decision-making and continuous improvement is an asset

• Knowledge of techniques and approaches to strategic planning

• Effective report writing, presentation and public relations skills

• Demonstrated strong solution-oriented leadership and strategic communications skills, project management, political acuity, diplomacy and well developed judgment when dealing with sensitive matters

• Effective facilitation, influencing and negotiation skills

• Proven ability to integrate internal and external resources to position successful outcomes

• Exceptional relationship building and conflict resolution skills

• Strong analytical skills with the ability to source and interpret data, identify trends, and translate insights into actionable strategies.

• Experience in developing and managing performance indicators and reporting systems to monitor progress and outcomes.

What We Offer

This full-time position is eligible for the following:

• Annual salary range: 178,588.00 - 223,235.00 (based on a 35-hour work week)

• Comprehensive benefits package

• Participation in the OMERS pension plan

• Paid time-off including vacation, incidental time and volunteer days

• Hybrid work environment

Visit the Town’s Employment page to learn more about what Milton offers.

Interested applicants should apply online at www.milton.ca under the Employment Opportunities section. This job posting will remain open until filled; application received by 11:59 pm on January 3, 2026 will be given first consideration.

If you are currently employed with the Town of Milton, please apply internally through the Jobs Hub app of your Workday account in order for your application to be processed as an internal applicant.

In accordance with the Freedom of Information and Privacy legislation, applicant information is collected under the authority of the Municipal Act and will be used strictly for candidate selection.