HM Note: This hybrid contract role is three (3) days in office. Candidates' resumes must include first and last name.

Description

Role Summary:

• Supply Ontario seeks an accomplished Senior IT Project Manager to lead the strategic implementation and execution of our Enterprise Technology transformation initiatives. This pivotal role will drive large-scale, complex technology projects that establish Supply Ontario's independent cloud infrastructure and modernize our digital ecosystem, ensuring alignment with organizational objectives while maintaining operational excellence throughout the transformation journey.
• The successful candidate will oversee multiple high-visibility initiatives including cloud migration, system integration, and platform modernization efforts. Working across organizational boundaries, this position requires exceptional leadership in navigating complex technical landscapes while delivering measurable business value. The role presents a unique opportunity to shape Supply Ontario's technological future through strategic program management, stakeholder engagement, and the delivery of transformative solutions that enhance service delivery for public sector procurement.

Required Skills:

• 7+ years' experience leading complex technical implementation programs, with demonstrated success in enterprise system deployments, cloud migrations, or digital transformation initiatives.
• 5+ years' experience managing multiple interdependent technical workstreams in high-visibility environments requiring rigorous coordination and stakeholder management.
• Deep expertise in technology governance, system integration, and platform migration with proven ability to navigate complex architectural dependencies.
• 5+ years' experience leading cross-functional technical teams across organizational boundaries while effectively communicating with executive leadership.

Responsibilities:

1. Strategic Program Leadership:

a. Lead large-scale, complex, high-profile technology transformation projects that establish Supply Ontario's enterprise technology foundation and enable business agility.

b. Drive end-to-end project lifecycle management for multiple concurrent initiatives, from inception through deployment and transition to operations.

c. Develop and maintain comprehensive project governance structures, ensuring effective decision-making, risk management, and alignment with enterprise standards.

d. Champion the adoption and adaptation of project management methodologies and frameworks suited to each project's unique requirements and organizational context.

2. Stakeholder Management and Communication:

a. Build and maintain strong relationships with executive leadership, providing regular updates on project progress, risks, and strategic recommendations.

b. Facilitate cross-functional collaboration between technology teams, business units, and external partners to ensure comprehensive requirements gathering and solution alignment.

c. Establish and participate in steering committees and stakeholder forums, effectively managing expectations and ensuring alignment with organizational goals.

d. Develop and execute strategic communication plans that ensure stakeholder engagement and buy-in throughout the project lifecycle.

3. Technical Planning and Execution:

a. Oversee the technical planning and implementation of enterprise technology solutions, ensuring scalability and alignment with architectural standards.

b. Coordinate with internal teams and external partners to establish robust testing, deployment, and support frameworks.

c. Ensure project deliverables meet business requirements on time, within scope, and aligned with quality standards.

d. Drive the development of project documentation, standard operating procedures, and knowledge transfer materials.

4. Resource and Team Management:

a. Source, select, and onboard multidisciplinary team members, clarifying roles and responsibilities while setting clear performance expectations.

b. Lead and mentor project teams, fostering collaboration and ensuring effective knowledge sharing across both internal staff and external consultants.

c. Resolve resourcing and interpersonal conflicts, negotiate changes to resource allocation, and ensure optimal team performance.

d. Develop and maintain detailed project schedules, resource plans, and capacity models across multiple workstreams.

5. Risk and Issue Management:

a. Proactively identify potential risk events and issues, developing comprehensive mitigation strategies before problems occur.

b. Articulate and prioritize risks at senior executive levels, recommending actionable mitigation strategies for decision-makers.

c. Implement robust monitoring and control mechanisms for project resources, timelines, and deliverables.

d. Integrate risk management within governance frameworks to align decisions with organizational risk appetite and standards.

6. Change Management and Adoption:

a. Develop and implement change management strategies to overcome resistance and capitalize on support throughout all project stages.

b. Drive organizational readiness activities, ensuring successful adoption of new technologies and processes.

c. Establish feedback mechanisms to measure adoption rates and user satisfaction, implementing improvements as needed.

d. Champion best practices and standards to facilitate quality control and adherence to methodologies.

7. Methodology Excellence and Standards:

a. Provide subject matter expertise and guidance on specific project management methodologies, ensuring consistent application across all initiatives.

b. Prepare training materials and deliver training sessions on project delivery methodology in accordance with organizational guidelines.

c. Acquire, customize, document, integrate, communicate and implement comprehensive IT standards and guidelines across the enterprise.

d. Lead methodology and development teams in self-organization, identifying and addressing gaps in frameworks while maintaining a safe working environment. e. Mentor and coach teams on removing impediments, supporting product owners, and providing education where needed to ensure methodological excellence.

8. Performance Monitoring and Optimization:

a. Establish key performance indicators to measure project success and business value realization.

b. Provide comprehensive project reporting to multi-stakeholder audiences at senior executive levels.

c. Monitor and forecast project progress, ensuring targets are met while maintaining fiscal accountability.

d. Lead post-implementation reviews and optimization initiatives to ensure continuous improvement.

General Skills:

• Project Leadership: Proven experience leading organizational development, strategy development, and business planning for large-scale technology initiatives.
• Strategic Planning: Demonstrated ability to develop and execute comprehensive implementation strategies aligned with organizational objectives.
• Stakeholder Management: Excellence in managing relationships with executive leadership, cross-functional teams, and external partners in complex multi-stakeholder environments.
• Technical Acumen: Strong understanding of enterprise technology architecture, cloud platforms, integration patterns, and modernization best practices.
• Enterprise Architecture: Knowledge and experience with Information and Information Technology (I&IT) methods and techniques associated with the development and implementation of enterprise architecture frameworks.
• Risk Management: Expertise in identifying, assessing, and mitigating project risks throughout the implementation lifecycle.
• Change Management: Proven track record in leading organizational change initiatives and ensuring successful technology adoption.
• Communication: Outstanding verbal and written communication skills, with experience presenting to executive leadership and diverse stakeholder groups. Strong facilitation, negotiation, and consensus building capabilities.
• Problem-Solving: Strong analytical and critical thinking skills, with the ability to navigate complex technical and organizational challenges.
• Methodology Expertise: Deep knowledge of project management methodologies and ability to adapt approaches based on project requirements. Demonstrated experience in specific methodology implementation and ability to educate others.
• Team Dynamics Management: Experience managing relationships between methodology teams and product owners, maintaining safe working environments, and facilitating conflict resolution.
• Coaching and Mentoring: Experience mentoring and coaching teams on removing impediments, with proven ability to support product owners and provide education where needed.
• Quality Focus: Commitment to delivering high-quality solutions that meet enterprise standards and user needs.

Deliverables:

Program Management Deliverables:

• Enterprise Technology Implementation Strategy
• Comprehensive program roadmap and implementation plan
• Project charter and governance framework documentation
• Stakeholder engagement and communication strategy
• Risk management framework and mitigation plans
• Resource allocation and capacity planning models
• Cloud Migration and Modernization
• Migration strategy and phased approach documentation
• Application assessment and prioritization framework
• Technical transition plans and cutover procedures
• Testing and validation protocols
• Post-migration optimization recommendations
• Integration and Architecture
• Enterprise integration framework and standards
• System interface specifications and documentation
• Data flow and dependency mapping
• Architecture decision records and design patterns
• Performance benchmarking and optimization plans
• Governance and Compliance
• Project governance structures and procedures
• Compliance assessment and remediation plans
• Quality assurance frameworks and checkpoints
• Technical review board documentation
• Standards adherence and audit reports

Cross-Program Deliverables:

• Status and Reporting
• Executive dashboards and status reports
• Risk and issue logs with mitigation strategies
• Budget tracking and variance analysis
• Milestone achievement and progress metrics
• Stakeholder communication materials
• Change Management
• Organizational change management plans
• Training and enablement strategies
• Communication plans and materials
• Adoption metrics and success criteria
• Feedback incorporation and improvement plans
• Knowledge Transfer
• Project documentation and repositories
• Lessons learned and best practices documentation
• Standard operating procedures
• Handover and transition plans
• Team capability development materials

Desirable Skills:

• Certifications: Professional certifications such as PMP, PgMP, MSP, or equivalent project/program management credentials.
• Methodology Certifications: Project methodology certifications such as Agile Coach, Certified Scrum Master (CSM), SAFe Program Consultant (SPC), or Lean Six Sigma Black/Green/Yellow Belt.
• Public Sector Experience: Understanding of government technology implementation requirements, procurement processes, and governance frameworks.
• Cloud Platforms: Experience with cloud migrations and deployments, particularly in Azure or similar enterprise cloud environments.
• Agile Methodologies: Experience with Agile, SAFe, or hybrid project management approaches in enterprise implementations.
• Enterprise Systems: Knowledge of enterprise resource planning, procurement systems, or similar large-scale business applications.
• Data Management: Understanding of data governance, migration strategies, and analytics platform implementations.
• Security and Compliance: Knowledge of security frameworks, privacy requirements, and regulatory compliance in technology implementations.
• Vendor Management: Experience managing relationships with technology vendors, system integrators, and consulting partners.
• Financial Management: Advanced skills in project financial management, including multi-year budgeting and complex funding models.
• Emerging Technologies: Awareness of emerging technology trends and their application to enterprise transformation initiatives.

Must Haves:

• 7+ years' experience leading complex technical implementation programs, with demonstrated success in enterprise system deployments, cloud migrations, or digital transformation initiatives.
• 5+ years' experience managing multiple interdependent technical workstreams in high-visibility environments requiring rigorous coordination and stakeholder management.
• 5+ years experience Deep expertise in technology governance, system integration, and platform migration with proven ability to navigate complex architectural dependencies.
• 5+ years' experience leading cross-functional technical teams across organizational boundaries while effectively communicating with executive leadership