Senior Project Manager, Financial Reporting & Data Modernization (Insurance Client)- 1689

S.I. Systems Ltd.; Toronto, London, Winnipeg; Hybrid; CAD 110,000 - 150,000; Full time

Job summary

S.I. Systems Ltd. is seeking a Senior Project Manager to lead Financial Reporting Modernization initiatives for an Insurance client.

You will manage complex, multi-workstream programs within the Technology PMO, coordinating discovery, requirements and governance to deliver an executable roadmap. The role focuses on discovery, MVP scoping, stakeholder alignment and interfacing with external consulting (Electric Mind).

Qualifications

• 5–10 years of experience leading large, complex projects with multiple workstreams.
• PMP or equivalent certification required.
• Strong planning, governance and requirements management skills.
• Deep understanding of PDLC and project governance frameworks.

Responsibilities

• Develop and maintain integrated project plans, milestones, dependencies, risks and issues.
• Coordinate discovery and requirements across business, technology, data and security.
• Facilitate agreement on scope, MVP and phased delivery roadmap.
• Coordinate estimation activities with SMEs, architecture, data and delivery teams.
• Manage dependencies between initiatives and external engagements.
• Establish governance forums and reporting mechanisms for the initiative.
• Drive stakeholder alignment and resolution of scope/timeline/cost escalations.
• Coordinate external vendors and consulting teams to align with objectives.
• Prepare executive updates outlining progress, risks and decisions.
• Apply project delivery discipline to support readiness and delivery within budgets.

Skills

Project management

Stakeholder management

Planning & governance

Communication

Leadership

Education

PMP certification

Tools

MS Project

Jira

Confluence

SharePoint

Job description

Senior Project Manager, Financial Reporting & Data Modernization (Insurance Client)- 1689

Senior Project Manager, Financial Reporting & Data Modernization (Insurance Client)- 1689

Duration: 12 Months

Location: Toronto, London or Winnipeg (Hybrid, 3x/week)

Overview:

Our insurance client is seeking a Senior Project Manager to lead complex business and technology transformation initiatives within its Technology PMO, supporting the Workplace Benefits & Retirement (WBR), Digital, AI, Applications and Platforms, and Canadian Operations & Business Enablement portfolio.

The initial assignment will focus on Financial Reporting Modernization, working alongside the broader WBR Data Strategy initiative and an external consulting engagement with Electric Mind. The immediate priority is to bring structure to discovery and planning, align stakeholders and dependencies, and translate business requirements, architecture recommendations and data strategy outcomes into an executable roadmap.

The successful candidate will help mature the Initiative Brief, define the minimum viable product (MVP), coordinate requirements and estimates, and establish the governance and investment materials needed to advance the initiative toward funding and delivery.

Responsibilities

• Develop and maintain integrated project plans, milestones, dependencies, risks, issues, assumptions and decision logs.
• Coordinate discovery and requirements gathering across business, technology, data, architecture, security and operational stakeholders.
• Facilitate agreement on scope, MVP, target outcomes and a phased delivery roadmap.
• Coordinate estimation activities with business subject matter experts, architecture, data and delivery teams.
• Manage planning dependencies between Financial Reporting Modernization, the broader WBR Data Strategy and the Electric Mind engagement.
• Ensure relevant consulting recommendations, target-state architecture and modernization opportunities are assessed and incorporated into project requirements, estimates and delivery plans.
• Develop and maintain the Initiative Brief and supporting materials for intake, seeding, gating, funding and governance approvals.
• Establish governance forums, working groups, steering committees and reporting mechanisms appropriate to the initiative.
• Drive stakeholder alignment, resolve competing priorities and escalation decisions affecting scope, timelines, costs or delivery readiness.
• Coordinate external vendors and consulting teams, ensuring their activities and recommendations align with business objectives and project milestones.
• Prepare executive updates that clearly communicate progress, risks, dependencies, recommendations and decisions required.
• Apply project delivery discipline and change leadership to support business readiness and delivery within agreed timelines and budgets.

Must Haves

• 5 to 10 years of experience managing large, complex projects with multiple workstreams, including digital transformation, software implementations, integrations and data migration.
• PMP or equivalent certification.
• Strong project planning, requirements management and governance skills, with the ability to bring structure to ambiguous initiatives.
• Deep understanding of the Project Delivery Life Cycle (PDLC) and project governance frameworks.
• Proven ability to lead cross-functional teams and coordinate business, technology, architecture, data and external partners.
• Experience influencing senior leaders and managing executive stakeholders, including communications, negotiations and competing priorities.
• Strong business relationship and change management skills, with the ability to simplify complex situations and drive outcomes in a fast-paced environment.
• Excellent written, verbal, presentation and facilitation skills, including translating technical concepts into clear business language for executive audiences.
• Strong strategic thinking, decision-making and problem-solving skills, balancing client needs with business and technology expectations.
• Ability to accommodate flexible schedules when required.

Nice to Haves

• Experience with financial reporting, data modernization, insurance, benefits administration or large-scale business transformation initiatives.
• Experience with digital platforms, AI, cloud technologies and data-driven solutions.
• Experience delivering projects with enterprise-wide impact.
• Experience mentoring project managers and developing high-performing teams.
• Advanced knowledge of Agile, Waterfall and Iterative methodologies, and tools such as MS Project, Jira, Confluence and SharePoint.
• Additional credentials such as PMI-PBA, PMI-ACP, Certified ScrumMaster or SAFe Agilist.
• Bilingual proficiency in English and French.

Disclaimer:

AI may be used in evaluating candidates.

This posting is for an existing vacancy.