Sr. Project Manager – Enterprise Application Integration – Bill 64 / Law 25 Data Retention and Disposition – Insurance

S.I. Systems Ltd.; Toronto, Winnipeg; Hybrid; CAD 120,000 - 150,000; Full time

Job summary

S.I. Systems Ltd. is seeking three Senior Project Managers to lead enterprise application integration for a major Bill 64 / Law 25 data retention and disposition program in the insurance sector.

The role requires coordinating with a Delivery Manager in the Technology PMO, program management, and external partners. The program covers ~350 enterprise applications with an 18–24 month horizon. You will own delivery for assigned projects, manage budgets and risks, and drive compliance across security

Qualifications

• 7+ years in project management leading software implementations.
• 5+ years in projects with integrations, data migration or complex tech environments.
• 5+ years leading project teams with coaching/feedback.
• Strong understanding of enterprise app complexity and integration dependencies.
• Strong stakeholder leadership and vendor coordination.
• Excellent presentation and written communication for executive audiences.

Responsibilities

• Lead projects from initiation through implementation and closure using established frameworks.
• Create integrated plans with application teams and the implementation partner, aligning milestones and resources.
• Coordinate onboarding and integration activities, clarifying interface requirements and delivery risks.
• Establish budgets, forecasts, monitor resource burn rates and variances.
• Maintain project charters, RAID logs, financial summaries, and cutover plans.
• Prepare dashboards, program scorecards and executive progress reports.

Skills

Enterprise apps

APIs & batch

Stakeholder leadership

Vendor coordination

Budgeting & forecasting

Risk & issue mgmt

Executive comms

Scrum/Agile meetings

Tools

SAP

Job description

Sr. Project Manager – Enterprise Application Integration – Bill 64 / Law 25 Data Retention and Disposition – Insurance

Sr. Project Manager – Enterprise Application Integration – Bill 64 / Law 25 Data Retention and Disposition – Insurance

Duration: 12 Months

Overview:

Our client, a large insurance organization, is seeking three Senior Project Managers to lead application integration workstreams within its Bill 64 / Québec Law 25 data retention and disposition program. The mandate supports compliance through the delivery of automated retention and disposition capabilities across the enterprise application estate. Reporting to a Delivery Manager within the Technology PMO, you will work closely with the Program Manager, application teams, business stakeholders and an external implementation partner.

The program is replacing manual retention and disposition activities with an automated solution. Approximately 350 enterprise applications will be connected to the solution in waves over an anticipated 18–24-month program horizon. Integration approaches may include APIs, batch files and other interfaces suited to each application.

You will own delivery for assigned projects and application groups, coordinating technical dependencies, resources, financials and implementation readiness. Success requires strong enterprise application delivery experience, sound technical comprehension and a proactive approach to resolving issues in a fast-paced environment.

Responsibilities:

• Lead assigned projects from initiation through implementation and closure, following established application delivery, project management and governance frameworks.
• Build and maintain integrated plans with application teams and the implementation partner, aligning milestones, dependencies, resources and vendor deliverables.
• Coordinate application onboarding and integration activities, ensuring teams understand interface requirements, technical dependencies and delivery risks.
• Establish budgets and forecasts; monitor resource consumption, burn rates and variances, and address impacts to scope, cost and schedule.
• Maintain project charters, stakeholder matrices, RAID logs, financial summaries, implementation and cutover plans, and other required delivery documentation.
• Identify risks and remove delivery roadblocks early, working across organizational boundaries and escalating issues with clear impacts and recommended actions.
• Lead focused project meetings and scrums; document decisions, assign actions and maintain clear accountability across internal teams and external partners.
• Prepare concise dashboards, program scorecards and executive presentations covering delivery progress, financials, resource needs and decisions required.
• Manage scope changes and approvals, maintaining traceability of their impacts on timelines, budgets, resources and business outcomes.
• Partner with security, risk and compliance teams to complete required assessments and align delivery with Bill 64 / Law 25 requirements, internal cyber and technology controls, and approved retention and disposition policies.
• Coordinate change management, implementation readiness and any required decommissioning activities; conduct post-implementation reviews and share lessons learned.

Must haves:

• Minimum 7+ years of project management experience leading software implementations.
• Minimum 5 years of experience managing projects involving integrations, data migration or complex technical environments.
• Minimum 5 years of experience managing project teams, including providing coaching and/or feedback to resources.
• Strong understanding of enterprise application complexity, architecture and integration dependencies, with the ability to engage technical teams on approaches such as API and batch interfaces.
• Strong stakeholder leadership and vendor coordination skills, with the ability to navigate complex organizations and maintain delivery momentum with limited supervision.
• Strong project planning, financial management, risk and issue management, and change control capabilities.
• Excellent presentation, meeting facilitation and written communication skills, including translating complex technical topics into concise business terms for executive audiences.
• A proactive, organized and accountable working style, with the ability to mobilize quickly, manage changing priorities and tight deadlines, and simplify ambiguous situations.

Nice to have:

• PMP certification.
• Experience delivering projects in insurance, banking or another complex financial services environment.
• Experience with project planning and delivery management tools.
• Experience with SAP cloud or on-premises environments, or broader business transformation initiatives.

Sr. Project Manager – Enterprise Application Integration – Bill 64 / Law 25 Data Retention and Disposition – Insurance

Duration: 12 Months

Location: Toronto (Hybrid, 3x/week)

Overview:

Our client, a large insurance organization, is seeking three Senior Project Managers to lead application integration workstreams within its Bill 64 / Québec Law 25 data retention and disposition program. The mandate supports compliance through the delivery of automated retention and disposition capabilities across the enterprise application estate. Reporting to a Delivery Manager within the Technology PMO, you will work closely with the Program Manager, application teams, business stakeholders and an external implementation partner.

The program is replacing manual retention and disposition activities with an automated solution. Approximately 350 enterprise applications will be connected to the solution in waves over an anticipated 18–24-month program horizon. Integration approaches may include APIs, batch files and other interfaces suited to each application.

You will own delivery for assigned projects and application groups, coordinating technical dependencies, resources, financials and implementation readiness. Success requires strong enterprise application delivery experience, sound technical comprehension and a proactive approach to resolving issues in a fast-paced environment.

Responsibilities:

• Lead assigned projects from initiation through implementation and closure, following established application delivery, project management and governance frameworks.
• Build and maintain integrated plans with application teams and the implementation partner, aligning milestones, dependencies, resources and vendor deliverables.
• Coordinate application onboarding and integration activities, ensuring teams understand interface requirements, technical dependencies and delivery risks.
• Establish budgets and forecasts; monitor resource consumption, burn rates and variances, and address impacts to scope, cost and schedule.
• Maintain project charters, stakeholder matrices, RAID logs, financial summaries, implementation and cutover plans, and other required delivery documentation.
• Identify risks and remove delivery roadblocks early, working across organizational boundaries and escalating issues with clear impacts and recommended actions.
• Lead focused project meetings and scrums; document decisions, assign actions and maintain clear accountability across internal teams and external partners.
• Prepare concise dashboards, program scorecards and executive presentations covering delivery progress, financials, resource needs and decisions required.
• Manage scope changes and approvals, maintaining traceability of their impacts on timelines, budgets, resources and business outcomes.
• Partner with security, risk and compliance teams to complete required assessments and align delivery with Bill 64 / Law 25 requirements, internal cyber and technology controls, and approved retention and disposition policies.
• Coordinate change management, implementation readiness and any required decommissioning activities; conduct post-implementation reviews and share lessons learned.

Must haves:

• Minimum 7+ years of project management experience leading software implementations.
• Minimum 5 years of experience managing projects involving integrations, data migration or complex technical environments.
• Minimum 5 years of experience managing project teams, including providing coaching and/or feedback to resources.
• Strong understanding of enterprise application complexity, architecture and integration dependencies, with the ability to engage technical teams on approaches such as API and batch interfaces.
• Strong stakeholder leadership and vendor coordination skills, with the ability to navigate complex organizations and maintain delivery momentum with limited supervision.
• Strong project planning, financial management, risk and issue management, and change control capabilities.
• Excellent presentation, meeting facilitation and written communication skills, including translating complex technical topics into concise business terms for executive audiences.
• A proactive, organized and accountable working style, with the ability to mobilize quickly, manage changing priorities and tight deadlines, and simplify ambiguous situations.

Nice to have:

• PMP certification.
• Experience delivering projects in insurance, banking or another complex financial services environment.
• Experience with project planning and delivery management tools.
• Experience with SAP cloud or on-premises environments, or broader business transformation initiatives.