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About the Role

The Director, Systems & Data Transformation is accountable for shaping and executing HSB Canada’s enterprise systems, data, and digital transformation agenda. This role acts as a strategic partner to the CEO and Executive Leadership Team, translating business priorities into an integrated multi-year roadmap and leading complex cross-functional programs to deliver measurable improvements.

Responsibilities

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; escalate decisions with clear options and recommendations.
Define measurable outcomes and key performance indicators, using performance insights to continuously improve delivery and business value.
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.
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.
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.
Build, lead, coach, and retain a high-performing multidisciplinary team spanning business systems analysis, product and application leadership, data engineering, analytics, and data science.
Define clear mandates, decision rights, accountabilities, delivery standards, and career pathways; create a culture of ownership, collaboration, inclusion, innovation, and continuous learning.
Develop workforce and sourcing strategies that balance internal capability, global partnerships, and external expertise while managing capacity and succession risk.
Serve as a trusted advisor translating complex system and data topics into clear choices, trade-offs, recommendations, and decisions.
Build alignment across Canadian and global stakeholders, facilitate executive governance, and communicate progress, risks, investment needs, and realized outcomes with clarity.
Lead organizational change and adoption for new capabilities, and bring external perspective, emerging practices, and market insight to continuously evolve HSB Canada’s business and technology environment.

Requirements

University-level education in computer science, business administration, risk management, or equivalent professional experience.
8–12 years demonstrated experience in business, technology, or product roles; insurance or broader financial services.
Structured, hypothesis-driven problem solving: ability to frame ambiguity, develop options, assess trade-offs, and drive to clear decisions.
Strong analytical capability: extracting insights from data and market research and translate them into strategy and action.
Multi-workstream leadership: proven ability to manage multiple initiatives in parallel while maintaining quality, pace, and stakeholder alignment.
Executive communication: ability to produce crisp, compelling materials and present complex topics simply and persuasively to senior audiences.
Strong P&C insurance (or broader financial services) product knowledge—coverage/wordings, underwriting appetite, pricing fundamentals, and regulatory considerations is an asset.
Experience building ecosystems/partnerships (vendors, data providers, technology partners) to enable product and service innovation is an asset.

Skills

Guidewire platform
Quote, Bind and Issue (QBI)
Data Science
Responsible AI
Enterprise data strategy
Data governance
Data quality
Data architecture
Data platforms
Analytics
Business systems analysis
Product leadership
Application leadership
Data engineering

Location

Toronto

Work Type

Hybrid

Experience Level

8-12 years

Education Level

University-level education in computer science, business administration, risk management, or equivalent professional experience

Salary/Compensations

$159,000 - $186,000 per year plus annual company bonus

Benefits

Engaging and collaborative environment that promotes continuous learning and development
Hybrid work environment
Great compensation package including an annual company bonus
Competitive company-paid flexible health and dental benefits, starting on your first day
Flexible dollars provided by the company to put towards a Health Spending Account and/or Wellness Spending Account
Wellness program with tools and resources supporting your mental, physical, and financial wellbeing
Participation in the DC Pension Plan with a progressive employer contribution scale based on tenure
Optional company match in the RRSP plan
Generous time off including vacation, personal days, unplanned time, Statutory Holidays and company-wide early closure half-days
Learning and development programs and resources, including unlimited access to LinkedIn Learning, Education Assistance Program, and reimbursement for professional fees
Employee Referral Program and Recognition Program

About the Company

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 stable 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.

Equal Opportunity

HSB Canada is committed to providing a work environment that is inclusive and free of employment barriers and discrimination. Accommodations will be made for qualified applicants with a disability throughout the recruitment process. If you receive a request for an interview and you have a disability which will require an accommodation to support your participation, please consult with Human Resources or contact hr@hsb.ca as soon as practical so that suitable accommodations can be arranged.
We do not use AI in our recruitment process - applications are reviewed by our team to ensure a fair and personalized experience.