Manager Digital Transformation

Town of Milton; Canada; On-site; CAD 122,000 - 154,000; Full time

Job summary

A progressive municipal organization in Canada seeks a Manager of Digital Transformation to oversee IT initiatives, lead technology innovation, and implement digital strategies for enhancing service delivery. The successful candidate will have a strong background in Information Technology with leadership experience and be skilled in managing cross-functional projects. This role offers a competitive salary and comprehensive benefits package, including flexible work arrangements and participation in the OMERS pension plan.

Benefits

Comprehensive benefits package

Discount on Active Living Pass

Flexible work arrangements

Qualifications

• 5+ years of experience in Information Technology, with 3+ years in a managerial role focused on digital transformation.
• Experience in municipal or public sector environments.
• Hands-on experience in managing large-scale digital transformation projects.

Responsibilities

• Lead digital transformation initiatives and manage technology projects.
• Collaborate with stakeholders to define technology requirements.
• Develop and execute a comprehensive digital transformation strategy.

Skills

Leadership

Project Management

Cross-functional collaboration

Financial acumen

Problem-solving

Critical thinking

Communication skills

Agile methodologies

Education

Post-secondary degree in Information Technology, Computer Science, or Business Administration

Project Management Professional (PMP) certification

ITIL certification

Change Management certification

Tools

Cloud platforms

Data analytics tools

Job description

Job Type: Permanent

Department:

Salary: $122,588.00 - $153,234.00

Close Date (closes at 12:00 am on date noted below):

March 18, 2026

Hours per Week: 35

Openings: 1

Position Summary

About Milton

Join one of Ontario’s fastest-growing and most dynamic municipalities. The Town of Milton is proud to deliver high-quality, sustainable municipal services that support a vibrant, inclusive, and forward-looking community where residents thrive, businesses succeed, and nature is respected and protected.

Our vision is to foster a safe, diverse, and welcoming environment—one that honours its natural landscapes and rich heritage, supports thriving and inclusive neighbourhoods, nurtures a strong and balanced economy, and offers exceptional opportunities to live, learn, work, and play.

What We Offer?

This position is eligible for the following:

• Annual Salary Range: $122,588 - $153,234
• Benefits: Regular full-time employees receive a comprehensive benefit package, with all premiums paid by the Town, an Employee Assistance Program, top-up maternity/parental leave benefits and life insurance.
• Eligibility to participate in the OMERS pension plan
• Paid time off, including vacation, incidental and volunteer days
• Employee perks/discounts: Discount on Active Living Pass and Perkopolis
• Flexible work arrangements, including hybrid work options and participation in the Town’s compressed work-week program (for eligible positions)
• For further details of what we offer, please visit Why Milton

Position Summary

Reporting to the Director, Information Technology, the Manager, Digital Transformation will lead the planning, execution, and oversight of digital transformation initiatives within the Information Technology (IT) team and across the broader organization. This individual will drive technological innovation, optimize IT infrastructure, improve processes, and implement technology solutions that enhance service delivery for citizens and internal operations. The role involves strategic leadership, cross-functional collaboration, and the ability to manage large-scale technology projects while ensuring fiscal responsibility and operational efficiency.

Major Job Responsibilities

Strategy & Planning

• Assist with the development and execution of a comprehensive digital transformation strategy that aligns with the municipality’s goals, vision, and budget.
• Prioritize and advocate for digital initiatives that provide the greatest value to the organization, leveraging data-driven insights, stakeholder input, and industry best practices.
• Collaborate with senior leadership, department heads, and stakeholders to define technology requirements and transform business processes.
• Identify emerging technology trends, assess their potential impact, and recommend strategic initiatives to modernize municipal services.
• Establish measurable goals and KPIs for digital transformation projects, ensuring alignment with long-term municipal objectives.
• Develop and maintain a comprehensive digital roadmap for municipal IT systems, ensuring it evolves in alignment with technological advancements, community needs, and organizational priorities.
• Facilitate stakeholder engagement sessions to gather input, assess needs, and drive consensus on digital transformation priorities, ensuring all departments are aligned with the digital vision and strategy.

Acquisition & Development

• Assist with the evaluation, selection, and procurement of new digital technologies and systems to support technology modernization efforts.
• Oversee the deployment and integration of technology solutions across various departments, ensuring minimal disruption to services.
• Ensure that new systems and platforms are implemented with appropriate user training, support, and change management.
• Ensure robust data governance and security practices are incorporated into the deployment of new technologies, safeguarding municipal data and complying with relevant regulations and standards.

Operational Management

• Provide leadership in managing the daily operations of digital transformation projects, including overseeing timelines, resources, and project milestones.
• Manage the deployment and integration of new technologies, ensuring they enhance municipal operations, improve efficiency, and align with strategic goals.
• Assess proposed digital projects for feasibility, impact, and alignment with organizational goals, ensuring they contribute to improved efficiency, service delivery, and innovation.
• Work closely with the IT team to ensure implemented systems are optimized for performance, scalability, and security.
• Monitor and ensure the effective use of technology within the organization, addressing operational issues and user concerns promptly.
• Create and manage the project portfolio, balancing short- and long-term initiatives and prioritizing projects that deliver maximum value to the municipality.
• Establish and enforce IT governance frameworks to ensure that digital transformation initiatives are compliant with legal, security, and regulatory requirements.
• Manage post-deployment support and continuous improvement cycles, ensuring that implemented systems and technologies are regularly reviewed and updated to enhance efficiency and user satisfaction.

Fiscal Accountability

• Develop and manage budgets for digital transformation projects, ensuring adherence to financial constraints and optimizing resource allocation.
• Conduct cost-benefit analyses for digital initiatives and provide regular reporting on the status of digital projects, including cost, time, and scope.
• Implement financial controls and processes to track expenditures and ensure fiscal responsibility while driving cost-efficient solutions.
• Identify funding opportunities, grant possibilities, and other resources to support digital transformation goals.

Education & Experience

Minimum Qualifications

• Post-secondary degree in Information Technology, Computer Science, Business Administration, or a related field.
• 5+ years of experience in Information Technology, with at least 3 years in a leadership or managerial role focused on digital transformation.
• Experience working within municipal or public sector environments, understanding government processes, compliance frameworks, and the unique challenges of public service delivery.
• Demonstrated expertise in managing cross-functional projects using methodologies like Agile, Scrum, or Waterfall, along with a strong ability to collaborate with diverse stakeholders, including elected officials, department heads, and community representatives.
• Hands-on experience leading large-scale digital transformation projects, including modernizing and integrating technologies into legacy systems, implementing emerging technologies (e.g., cloud solutions, data analytics, IoT), and driving organizational change.
• Experience executing digital strategies aligned with organizational goals, identifying opportunities for process optimization and introducing innovative solutions to enhance citizen services and operational efficiency.
• Experience in developing and executing change management strategies to ensure smooth adoption of new technologies and processes across diverse departments and user groups.
• Project Management Professional (PMP) or equivalent certification
• ITIL (Information Technology Infrastructure Library) certification
• Certification in Change Management (Prosci or CCMP)
• Ability to execute digital transformation strategies aligned with municipal goals, while analyzing complex systems and identifying opportunities for innovation and efficiency.
• Working knowledge of modern IT systems (e.g., cloud platforms, data analytics, cybersecurity) and awareness of emerging technologies relevant to public sector innovation (e.g., IoT, AI, smart city solutions).
• Strong financial acumen and experience managing budgets for large-scale IT projects.
• Skills in managing organizational change, fostering a digital-first culture, and guiding teams through transitions to new technologies and processes.
• Outstanding written and verbal communication skills, with the ability to present complex ideas clearly to non-technical stakeholders.
• Strong problem-solving and critical-thinking abilities.

Preferred Qualifications

• Master’s degree in a relevant field (e.g., MBA, Master of Information Systems, etc.).
• 10+ years direct management experience overseeing digital transformation initiatives within a Government or Public Sector environment.
• Experience driving enterprise-wide technology adoption, including leading cultural change initiatives, improving digital literacy among staff, and successfully managing multi-year digital roadmaps across multiple municipal departments.
• Proven track record in leveraging advanced data strategies (e.g., open data platforms, predictive analytics) and implementing smart city technologies to improve public services, sustainability, and community engagement.
• Certified Digital Transformation Practitioner (CDTP)
• The Open Group Architecture Framework (TOGAF) certification
• Program Management Professional (PgMP) certification

Note to Applicants

This posting is for an existing job vacancy.

The Town is an equal opportunity employer, committed to fostering a diverse, inclusive, accessible, and respectful workplace. We encourage applications from all qualified individuals and are dedicated to fair and transparent hiring practices.

We thank all who apply, however only those selected to move forward in the process will be contacted.

Accommodations

Should you be selected to participate in the recruitment process, please inform Human Resources of any accommodations you may require. We will work with you to ensure your full participation in the process.

How to Apply

Interested applicants are invited to apply online at www.milton.ca under the Employment Opportunities section. Please ensure your application is submitted by 11:59 pm on March 17, 2026.

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.