Primary ObjectivesThe 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.
Job Responsibilities1. 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; escalate 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
5. Operating Model & People Leadership- 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
6. Advisory, Change Leadership & Influence- 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
Qualifications - 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
Company Benefits:We are pleased to offer our employees great benefits and resources to support their mental, physical and financial wellbeing. These include:
- An engaging and collaborative environment that promotes continuous learning and development
- A hybrid work environment that combines weekly in-office and remote days
- A 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 - on and off the job
- Participation in the DC Pension Plan with a progressive employer contribution scale based on tenure starting at 4%, plus 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
Our base salary range for this role is between $159000 to $186000 per year, plus an opportunity for an annual company bonus based upon a percentage of eligible pay. The salary estimate displayed represents the typical salary range for candidates hired in this position. Factors that may be used to determine your actual salary include your specific skills, how many years of experience you have and comparison to internal equity.
This role is located in our Toronto office on 390 Bay St, and we operate in a hybrid work model. This job posting is for an existing vacancy.
We do not use AI in our recruitment process - applications are reviewed by our team to ensure a fair and personalized experience.
