Primary Objectives

HSB Canada, part of Munich Re, is Canada's premier engineering-driven specialty insurer—bringing deep technical expertise to help clients stay ahead of complex, emerging, and technology-based risks. We blend specialty insurance with inspection, engineering, and technology-enhanced services to redefine what risk protection can be, with leading capabilities across areas such as cyber, equipment breakdown, renewable energy, and IoT technology services.

Backed by Munich Re, one of the world's most experienced and financially reliable insurance and reinsurance groups, HSB Canada combines global strength with deep knowledge of the Canadian market. Building on a long legacy of innovation and technical excellence, we continue to evolve our capabilities to address modern and emerging risks from cyber and artificial intelligence to connected technologies.

Job Responsibilities

The Director, Systems & Data Transformation is accountable for shaping and executing HSB Canada's enterprise systems, data, and digital transformation agenda. Acting as a strategic partner to the CEO and Executive Leadership Team, the Director translates business priorities into an integrated multi-year roadmap, leads complex cross-functional programs, and delivers measurable improvements in growth, customer and broker experience, operational effectiveness, decision-making, and risk management.

The role provides strategic and operational leadership for the transformation and optimization of the Guidewire ecosystem and its surrounding applications, integrations, data platforms, and controls, ensuring reliable and scalable support for policy, billing, claims, underwriting, and insurance operations.





The Director also leads the delivery of major business-facing capabilities, including Quote, Bind and Issue (QBI), underwriting workflow, digital experiences, enterprise data products, analytics, and responsible AI solutions, in close partnership with business, technology, operations, risk, and global stakeholders.

Success requires an enterprise-minded leader who can connect strategy, architecture, data, delivery, change management, and operational execution; build high-performing multidisciplinary teams; and establish the governance, partnerships, and performance disciplines needed to sustain transformation outcomes.

1. Transformation Strategy & Portfolio Delivery

- Define and maintain an integrated, multi-year systems, data, and digital transformation strategy aligned with enterprise priorities and target business outcomes
- Own the transformation portfolio from business case and prioritization through delivery, adoption, value realization, and transition to operations
- Establish portfolio governance, roadmaps, investment plans, budgets, resource capacity, milestones, benefits, and executive reporting
- Manage cross-program dependencies, delivery risks, organizational constraints, and competing priorities; accelerate decisions with clear options and recommendations
- Define measurable outcomes and key performance indicators,



using performance insights to continuously improve delivery and business value

2. Core Systems Transformation & Guidewire Leadership

- Set the strategy and roadmap for the specialty insurance technology ecosystem, balancing modernization, resilience, scalability, security, cost, and speed to market
- Provide accountable leadership for the Guidewire platform and surrounding applications, including architecture, configuration, integrations, data flows, environments, releases, and lifecycle management
- Lead major core-platform initiatives, including ClaimCenter transformation, while maintaining service continuity, production stability, support readiness, and effective control design

3. Digital Insurance & QBI Transformation

- Lead end-to-end delivery of Quote, Bind and Issue capabilities and underwriting workflow improvements in partnership with underwriting, product, operations, distribution, and technology teams
- Establish a scalable, reusable QBI architecture that supports multiple specialty products, distribution channels, evolving underwriting models, and integration with core platforms
- Champion underwriter-centered design, process simplification, automation, and adoption to improve experience, quality, and cycle time

4. Data Science & Responsible AI

- Define and mature HSB Canada's enterprise data and data science capabilities, including data strategy, governance, quality, architecture, platforms, and reusable data products
- Partner with business leaders to identify and deliver AI use cases across underwriting, claims, operations, finance, and distribution
- Ensure data and AI solutions are explainable, secure, measurable, and embedded into business processes and decisions

📌 Director, Systems (Toronto)
🏢 HSB Canada
📍 Toronto