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About the Role

The Consulting Director, Strategy & Transformation serves as a strategic partner to CNA Canada's executive leadership team, responsible for translating business strategy into executable plans and measurable outcomes. This role leads enterprise strategy execution, transformation initiatives, governance, and change management activities that enable business growth and operational effectiveness. Working across business units and enabling functions, the Director drives alignment, prioritization, accountability, and business readiness to ensure strategic initiatives deliver intended value.

Responsibilities

Lead the development, execution, and ongoing management of CNA Canada's strategic business plan, ensuring alignment between business objectives, initiatives, investments, resources, and measurable outcomes.
Facilitate annual planning, prioritization, and roadmap development activities to translate strategic priorities into executable plans and delivery commitments.
Partner with executive leadership to identify strategic opportunities, optimize operating models, and advance enterprise transformation priorities.
Lead cross-functional strategic and transformation initiatives, ensuring delivery against objectives, timelines, budgets, and expected business outcomes.
Establish governance, reporting, and performance management practices that support effective decision making, accountability, and enterprise alignment.
Monitor strategic initiatives, identify risks, dependencies, and barriers to execution, and recommend actions to maintain momentum and achieve results.
Drive business readiness, organizational change management, and stakeholder engagement activities to support successful implementation and adoption of strategic initiatives.
Facilitate collaboration across business units and enabling functions to improve organizational effectiveness, streamline processes, and maximize performance.
Conduct industry research, competitive analysis, and benchmarking to inform strategic recommendations and business decisions.
Develop executive-level presentations, assessments, business cases, and recommendations to support leadership discussions and decision making.
Define and monitor key performance indicators, reporting, and dashboard capabilities to measure strategic progress, business impact, and benefits realization.
Identify opportunities to leverage data, analytics, automation, artificial intelligence, and digital capabilities to enhance business performance and accelerate.

Requirements

Strong knowledge of the Property & Casualty insurance industry, including products, operations, and functional disciplines.
Demonstrated ability to lead enterprise-wide strategic and transformation initiatives involving multiple stakeholders and significant organizational change.
Strong executive presence and influencing skills with the ability to build alignment, challenge thinking, and effectively partner with senior leadership teams.
Exceptional strategic thinking, analytical, and problem-solving capabilities with the ability to translate complex issues into actionable recommendations.
Strong business and financial acumen, including experience evaluating investments, prioritizing initiatives, and measuring business value.
Excellent communication, facilitation, stakeholder management, and executive presentation skills.
Experience leading program management, governance, and organizational change initiatives.
Highly adaptable, results-oriented, and accountable, with the ability to manage multiple priorities in a dynamic environment.
Strong knowledge of Microsoft Office Suite and other enterprise business tools, including responsible use of AI-enabled technologies (such as Copilot or similar) to enhance efficiency, analysis and workflow in accordance with company policies.

Skills

Property & Casualty insurance industry knowledge
Strategic planning
Transformation initiative leadership
Executive influence
Program management
Governance
Organizational change management
Stakeholder management
Strategic thinking
Analytical skills
Problem-solving
Business acumen
Financial acumen
Communication skills
Facilitation skills
Executive presentation skills
Microsoft Office Suite
AI-enabled technologies

Location

Canada

Work Type

Full-time

Experience Level

Minimum 8 years of progressive experience in strategy, consulting, transformation, program management, or related business leadership roles.

Education Level

Bachelor's degree required
Master's degree or relevant professional designation preferred

Salary/Compensations

$135,000 - $170,000

Benefits

Comprehensive and competitive benefits package

About the Company

At CNA, we strive to create a culture in which people know they matter and are part of something important, ensuring the abilities of all employees are used to their fullest potential.
Our total rewards philosophy reflects our commitment to building a high-performing, inclusive culture where every team member is empowered to grow, contribute, and thrive.
We value the unique strengths and perspectives each individual brings to our business, our clients, and our communities.

Equal Opportunity

At CNA, we are committed to providing equal employment opportunities to all employees and applicants.
It is our policy to provide equal employment opportunities to employees and applicants based on job-related qualifications and ability to perform a job.
If you require an accommodation during the hiring process or upon hire, please inform Human Resources.
If a selected applicant requests accommodation during the recruitment process, CNA will consult with the applicant in order to provide suitable accommodation that takes into account the applicant’s accessibility needs.