Consulting Director, Business Strategy & Transformation

CNA Insurance; Toronto; On-site; CAD 135,000 - 170,000; Full time

Benefits offered by this job

Competitive benefits package

Job summary

CNA Canada is seeking a Consulting Director, Strategy & Transformation to partner with the executive team and translate strategy into actionable plans with measurable outcomes.

You will lead enterprise transformation, governance, and change management to enable growth and operational effectiveness across business units and functions.

Qualifications

• Bachelor's degree required; Master's degree preferred.
• Minimum 8 years of progressive experience in strategy, consulting, transformation, or related leadership roles.
• Property & Casualty insurance industry experience preferred; Commercial Lines experience is a plus.

Responsibilities

• Lead the development, execution, and ongoing management of CNA Canada's strategic business plan with clear alignment to objectives, initiatives, investments, and resources.
• Facilitate annual planning, prioritization, and roadmap development to translate priorities into executable plans and delivery commitments.
• Partner with executive leadership to identify strategic opportunities, optimize operating models, and advance transformation priorities.
• Lead cross-functional strategic initiatives ensuring delivery against objectives, timelines, budgets, and expected outcomes.
• Establish governance, reporting, and performance management to support decision making and alignment.
• Monitor initiatives, identify risks and barriers, and propose actions to maintain momentum and results.
• Drive business readiness, change management, and stakeholder engagement for successful implementation.
• Facilitate collaboration across units to improve effectiveness and streamline processes.
• Conduct industry research, benchmarking, and analysis to inform strategic recommendations.

Skills

Strategic thinking

Executive presence

Stakeholder management

Program leadership

Communication

Financial acumen

Education

Bachelor's degree

Master's degree preferred

Tools

Microsoft Office Suite

Copilot / AI tools

Job description

You have a clear vision of where your career can go. And we have the leadership to help you get there. 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. 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. Success in this role requires strong business acumen, executive influence, program leadership, and the ability to mobilize stakeholders around shared priorities while fostering a culture of execution, innovation, continuous improvement, and accountability.

Job Description: Essential Duties & 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 Reporting Relationship Typically AVP or above

Skills, Knowledge & Abilities

• 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.

Education & Experience

• Education & Experience Bachelor's degree required; Master's degree or relevant professional designation preferred.
• Minimum 8 years of progressive experience in strategy, consulting, transformation, program management, or related business leadership roles.
• Property & Casualty insurance experience strongly preferred; Commercial Lines experience considered an asset.
• Demonstrated experience partnering with executive leadership teams to drive strategic planning, organizational change, and enterprise transformation initiatives.

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.

The base salary range for this position is $135,000 - $170,000, complemented by a comprehensive and competitive benefits package to help our employees - and their family members - achieve their personal, financial, emotional, and social wellbeing goals.

Base salary determinations are based on various factors, including but not limited to, relevant work experience, skills, certifications and location.

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.

At CNA, we are focused on success, individually and collectively. We pride ourselves on promoting a culture that challenges and engages people. We strive to connect people, departments and business areas, to function as a team, and to serve our customers and communities with professionalism and respect. Our dedication to employee engagement, continuous learning and the open exchange of ideas is the cornerstone of our business.

These ideals, combined with our focus on the customer, enable us to explore new market opportunities and build on our success. Our values, culture and financial strength are what differentiates us from other employers and make CNA the place you want to work. At CNA, we are committed to advancing a culture of inclusion - one that attracts talent from all walks of life, foster respect and collaboration, and enables all of our colleagues to do their best work. At CNA, we have a long standing commitment to the diverse communities in which we live and work. We actively make a difference for the greater good through partnerships, sustainability, initiatives, and working together for a better tomorrow. Corporate Social Responsibility is not one person, or one department, it's the entire enterprise coming together to make the world a better place.