Senior Project Manager to lead an AI-enabled Intelligent Knowledge Management implementation and legacy system transition for our insurance client - 8946
S.I. Systems Ltd.
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Job summary
S.I. Systems Ltd. in Toronto is seeking a Senior Project Manager to lead an AI-enabled Intelligent Knowledge Management implementation and a legacy system transition for an insurance client.
You will oversee large, complex projects across multiple workstreams, delivering business outcomes within scope, schedule and budget. The role requires coordinating sponsors and stakeholders, applying Agile, Waterfall or hybrid methods, managing risks, and ensuring successful production readiness and
Qualifications
- 5+ years of experience leading complex, medium-to-large projects or programs involving multiple workstreams.
- Experience delivering digital transformation, software implementation, integration or data migration initiatives.
- Demonstrated ownership of project scope, schedules, budgets, financial forecasts, resources, risks and dependencies.
- Proven ability to influence senior and executive stakeholders, manage escalations and facilitate decisions across business and technology teams.
Responsibilities
- Lead projects from initiation to closure.
- Define scope, outcomes, priorities and delivery commitments with sponsors.
- Develop and maintain integrated project plans, schedules, budgets, resource plans and governance materials.
- Manage project financials, forecasting, risks, issues, dependencies and changes to scope or delivery commitments.
- Lead cross-functional teams, vendors and delivery partners.
- Facilitate steering committees and governance forums, communicate project health and escalates issues.
- Apply Agile, Waterfall or hybrid delivery methods in alignment with PDLC, governance and compliance requirements.
- Coordinate implementation readiness, business change impacts and transitions to production and operational support.
- Translate technical information into clear business implications, decisions and recommendations.
- Conduct post-implementation reviews, capture lessons learned, coach project teams and improve delivery practices.
Skills
Education
Tools
Job description
Senior Project Manager to lead an AI-enabled Intelligent Knowledge Management implementation and legacy system transition for our insurance client- 8946
Location:Toronto, Hybrid (3x/week)
Duration:14 Months
Start Date:November, 2026
Area: TPMO
Our insurance client is seeking a Senior Project Manager to lead large, complex initiatives involving multiple workstreams and significant business impact.
Working across business and technology teams, you will oversee the full project lifecycle for digital transformation, software implementation, integration and data migration initiatives. You will be accountable for delivering agreed business outcomes while managing scope, schedule, budget, quality, resources and risk.
- An AI centric project looking to enable Intelligent Knowledge Management.
- Transitioning from an older system to a new system.
- Lead projects from initiation and planning through implementation, production transition and closure.
- Partner with sponsors and senior stakeholders to define scope, business outcomes, priorities, success measures and delivery commitments.
- Develop and maintain integrated project plans, schedules, budgets, resource plans and governance materials.
- Manage project financials, forecasting, risks, issues, dependencies and changes to scope or delivery commitments.
- Lead cross-functional teams, vendors and delivery partners, coordinating workstreams and resolving competing priorities.
- Facilitate steering committees and governance forums, communicate project health, escalates issues and support informed decisions.
- Apply Agile, Waterfall or hybrid delivery methods in alignment with PDLC, governance and compliance requirements.
- Coordinate implementation readiness, business change impacts and transitions to production and operational support.
- Translate technical information into clear business implications, decisions and recommendations.
- Conduct post-implementation reviews, capture lessons learned, coach project teams and improve delivery practices.
- 5+ years of experience leading complex, medium-to-large projects or programs involving multiple workstreams.
- Experience delivering digital transformation, software implementation, integration or data migration initiatives.
- PMP or an equivalent project management certification.
- Demonstrated ownership of project scope, schedules, budgets, financial forecasts, resources, risks and dependencies.
- Proven ability to influence senior and executive stakeholders, manage escalations and facilitate decisions across business and technology teams.
- Experience coordinating cross-functional teams, vendors and delivery partners.
- Strong understanding of Agile, Waterfall and hybrid delivery, PDLC, project governance and risk management.
- Proficiency with project management and collaboration tools such as Microsoft Project, Jira, Confluence, Clarity and SharePoint.
- Strong business, technical and financial acumen, with excellent communication, facilitation, analytical and problem-solving skills.
- Ability to manage competing priorities and maintain delivery momentum in a fast-paced environment.
- Postsecondary education in Project Management, Business Administration or a related discipline, or equivalent experience.
- Additional certifications such as SAFe, PMI-ACP, PMI-PBA, CSM, PRINCE2, or other relevant Agile or Scrum credentials.
Senior Project Manager to lead an AI-enabled Intelligent Knowledge Management implementation and legacy system transition for our insurance client- 8946
Location:Toronto, Hybrid (3x/week)
Duration:14 Months
Start Date:November, 2026
Area: TPMO
Our insurance client is seeking a Senior Project Manager to lead large, complex initiatives involving multiple workstreams and significant business impact.
Working across business and technology teams, you will oversee the full project lifecycle for digital transformation, software implementation, integration and data migration initiatives. You will be accountable for delivering agreed business outcomes while managing scope, schedule, budget, quality, resources and risk.
- An AI centric project looking to enable Intelligent Knowledge Management.
- Transitioning from an older system to a new system.
- Lead projects from initiation and planning through implementation, production transition and closure.
- Partner with sponsors and senior stakeholders to define scope, business outcomes, priorities, success measures and delivery commitments.
- Develop and maintain integrated project plans, schedules, budgets, resource plans and governance materials.
- Manage project financials, forecasting, risks, issues, dependencies and changes to scope or delivery commitments.
- Lead cross-functional teams, vendors and delivery partners, coordinating workstreams and resolving competing priorities.
- Facilitate steering committees and governance forums, communicate project health, escalates issues and support informed decisions.
- Apply Agile, Waterfall or hybrid delivery methods in alignment with PDLC, governance and compliance requirements.
- Coordinate implementation readiness, business change impacts and transitions to production and operational support.
- Translate technical information into clear business implications, decisions and recommendations.
- Conduct post-implementation reviews, capture lessons learned, coach project teams and improve delivery practices.
- 5+ years of experience leading complex, medium-to-large projects or programs involving multiple workstreams.
- Experience delivering digital transformation, software implementation, integration or data migration initiatives.
- PMP or an equivalent project management certification.
- Demonstrated ownership of project scope, schedules, budgets, financial forecasts, resources, risks and dependencies.
- Proven ability to influence senior and executive stakeholders, manage escalations and facilitate decisions across business and technology teams.
- Experience coordinating cross-functional teams, vendors and delivery partners.
- Strong understanding of Agile, Waterfall and hybrid delivery, PDLC, project governance and risk management.
- Proficiency with project management and collaboration tools such as Microsoft Project, Jira, Confluence, Clarity and SharePoint.
- Strong business, technical and financial acumen, with excellent communication, facilitation, analytical and problem-solving skills.
- Ability to manage competing priorities and maintain delivery momentum in a fast-paced environment.
- Postsecondary education in Project Management, Business Administration or a related discipline, or equivalent experience.
- Additional certifications such as SAFe, PMI-ACP, PMI-PBA, CSM, PRINCE2, or other relevant Agile or Scrum credentials.
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