Primary Objectives:

HSB Canada is seeking a Vice President, Strategy & Innovation to help shape the company's long-term direction and turn strategic ambition into measurable business results. Reporting directly to the President & CEO and serving as a member of the Executive Leadership Team, this leader will bring quantitative rigor to enterprise strategy, strengthen execution discipline, and build a focused portfolio of innovation opportunities that create customer and business value.

Operating as an internal strategy and innovation consultant, the Vice President will work across business units and functions to frame complex issues, synthesize data and market insight, challenge assumptions, align senior stakeholders, and mobilize cross-functional teams. The role will also refresh HSB Canada's Internet of Things (IoT) strategy and go-to-market approach, strengthening the connection between technology-enabled services, insurance solutions, distribution opportunities, and customer needs.

The successful candidate will build strong cross-functional partnerships with HSB and Munich Re Group business leaders and enterprise partners to align priorities, remove barriers, and accelerate priorities ensuring understanding of relevant strategy, standards and philosophy.

Internal Applicants please apply online and submit your candidacy by October 14, 2026.

External Applicants please apply online and submit your candidacy by October 31,2026.

Job Responsibilities:

1. Enterprise Strategy and Strategic Planning
• Lead enterprise strategic planning with the President & CEO and Executive Leadership Team, including strategy refreshes, scenarios, priorities, and roadmaps.
• Shape evidence-based choices on growth, portfolio priorities, partnerships, investments, and emerging risks.
• Translate strategy into measurable objectives, initiatives, milestones, accountabilities, and resource priorities.
• Advise and challenge senior leaders, and develop clear Board materials on choices, trade-offs, progress, and decisions.

2. Business Performance and Execution Discipline
• Co-lead quarterly business reviews with FP&A, linking strategic priorities to financial and operating performance.
• Hold business leaders accountable for commitments, indicators, dependencies, corrective actions, and outcomes.
• Establish practical execution disciplines, including scorecards, governance, benefits tracking, and escalation.
• Use quantitative analysis to identify gaps, size opportunities, evaluate trade-offs, and recommend action, while respecting FP&A ownership of core financial processes.

3. Innovation Portfolio and Commercialization
• Build and manage an innovation portfolio aligned with strategy, customer needs, financial goals, risk appetite, and capacity.
• Identify and incubate new products, services, digital and data solutions, partnerships, and business models.
• Govern opportunities from validation and business case through pilot, commercialization, and value realization.
• Equip business leaders with disciplined innovation practices and recommend when to advance, pivot, pause, or stop initiatives.

4. IoT Strategy and Go-to-Market Leadership
• Refresh HSB Canada's IoT strategy, positioning, target segments, value propositions, ecosystem, and investment priorities.
• Develop a go-to-market roadmap linking IoT-enabled risk solutions to underwriting, distribution, client needs, service delivery, and value creation.
• Mobilize business, functional, and Group partners to move priority IoT opportunities from strategy to market.
• Define measures for adoption, customer value, risk improvement, revenue, and profitability.

5. Market Insight, Executive Advisory and Group Integration
• Turn customer, broker, competitor, technology, regulatory, and economic insights into actionable recommendations.
• Align HSB Canada, HSB, and Munich Re Group stakeholders around shared outcomes, decisions, and timelines.
• Lead high-priority cross-enterprise projects requiring structured problem solving, executive sponsorship, and coordinated execution.
• Deliver Board-ready communications, represent HSB Canada in Group forums, and translate Group capabilities into Canadian opportunities.

6.People Leadership
• Lead, coach, and develop up to five professionals across strategy, innovation, market insight, and portfolio management.
• Set clear priorities, delegate ownership, provide timely feedback, and hold the team accountable for results.
• Build diverse talent and foster curiosity, constructive challenge, experimentation, and learning.
• Influence and mobilize matrixed teams beyond direct reporting lines.

Qualifications:

Experience and Education
• Approximately 12 or more years of progressive experience in enterprise strategy, corporate strategy, management consulting, innovation, business transformation, corporate development, or a related field, including significant leadership experience.
• A record of advising CEOs and senior executives, leading enterprise planning, solving ambiguous business problems, and converting strategy into execution.
• Experience building and governing innovation portfolios and bringing products, services, or new ventures from insight through commercialization.
• Demonstrated people leadership, including coaching strong talent, setting priorities, and driving accountability across multiple concurrent workstreams.
• Prior experience with a leading management consulting firm is a strong asset.
• Experience in property and casualty insurance, reinsurance, or broader financial services is an asset; experience in another regulated, data-intensive sector may also be relevant.
• A bachelor's degree in business, economics, finance, engineering, mathematics, or a related discipline is required. An MBA or other relevant graduate degree is an asset.

Leadership Capabilities
• Strategic agility: Quickly grasps complex concepts, identifies the critical question, connects disparate information, and develops clear strategic choices.
• Quantitative and commercial acumen: Extrapolates insight from financial, operating, customer, and market data; builds robust business cases; and understands value drivers and trade-offs.
• Executive influence: Engages confidently with the Board, CEO, Executive Leadership Team, business-unit leaders, and Group stakeholders; constructively challenges senior colleagues while building trust and alignment.
• Execution orientation: Converts ideas into priorities, workplans, governance, milestones, and measurable outcomes; maintains momentum across multiple projects.
• Innovation leadership: Balances curiosity and experimentation with underwriting discipline, customer value, operational feasibility, regulatory considerations, and financial return.
• Communication excellence: Distils complex analysis into concise, compelling narratives and adapts communication for Board, executive, technical, and business audiences.
• Enterprise mindset: Optimizes for HSB Canada as a whole, navigates a matrixed global organization, and integrates diverse perspectives without losing pace or accountability.
• People leadership: Creates clarity, develops talent, fosters constructive debate, and builds a collaborative, high-performance culture.

Company Benefits:

Together, we engage with everything we have and are, to help humankind act braver and better. Go further with HSB.

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

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 a existing vacancy.

We do not use AI in our recruitment process - applications are reviewed by our team to ensure a fair and personalized experience.