Lead enterprise systems transformation at HSB Canada in Toronto, using Guidewire expertise and strategic data leadership within a hybrid work model.

As Director, Enterprise Systems Transformation, you will shape HSB Canada's multi-year systems, data, and digital agenda. Partner with the CEO and Executive Leadership Team while guiding core insurance platforms, digital capabilities, and responsible AI. Your leadership will connect architecture, delivery, governance, change management, and operational execution.

Key Responsibilities:

- Define integrated multi-year transformation strategy and roadmaps
- Lead portfolio governance, budgets, dependencies, risks, and executive reporting
- Direct Guidewire architecture, integrations, releases, and lifecycle management




- Deliver ClaimCenter transformation while maintaining service continuity
- Build multidisciplinary teams and establish delivery accountabilities

Requirements:

- University education or equivalent skilled experience
- Eight to twelve years in business, technology, or product roles
- Experience in insurance or broader financial services
- Structured problem solving and strong analytical capability
- Clear executive communication and multi-workstream leadership

Shape HSB Canada's enterprise transformation through Guidewire leadership, portfolio governance, data strategy, and executive partnership in Toronto.

📌 Director Enterprise Systems Transformation (Toronto)
🏢 HSB Canada
📍 Toronto