Director, Canada Strategy – Enablement

Jobtailor; Toronto; On-site; CAD 80,000 - 115,000; Full time

Job summary

Jobtailor in Toronto, Canada seeks an experienced strategy professional to conduct rigorous quantitative and qualitative analysis, shape priority recommendations, and develop board and public strategy documents. You will engage senior executives, collaborate across teams, and drive strategic projects with disciplined problem framing and execution.

The role emphasizes financial modeling, stakeholder management, and clear communication.

Qualifications

• Minimum 4 years of relevant business experience.
• University degree in business administration, finance, economics, engineering, or related discipline.
• Experience in management consulting, corporate strategy, a startup, as a Chief of Staff, or an equivalent role.
• Experience managing and collaborating directly with very senior stakeholder groups, including C-Suite and Senior Vice Presidents.
• Strong conceptual problem-solving skills, including structuring business problems, formulating and testing hypotheses, and developing recommendations.
• Strong analytical skills and proficiency in financial modelling tools and techniques, especially Excel.
• Ability to conduct quantitative and qualitative analysis and interpret and synthesize results.
• Experience conducting in-depth secondary research; primary research experience is an asset.
• Excellent oral and written communication and presentation skills.
• Ability to prepare formal business reports and presentations using PowerPoint.
• Strong interpersonal and stakeholder management skills.
• Strong project management skills and ability to prioritize and organize work effectively under tight timelines.
• High attention to detail.
• Strong, preferably expert, knowledge of Microsoft Office products including Excel, PowerPoint, and Word.
• Experience in insurance, health, wealth, or financial services is a plus but not required.
• Experience in digital strategy and transformation is an asset.
• Bilingualism in French and English, oral and written, is required for Quebec only

Responsibilities

• Conduct quantitative and qualitative research and analysis independently.
• Prepare and deliver recommendations on priority strategic questions for the Canadian Business.
• Develop and syndicate board and public-facing strategy documents.
• Engage executive stakeholders.
• Collaborate with strategy team members and partners across the business.
• Support delivery of strategic projects through workstream management, problem definition and structuring, cross-functional collaboration, updates, and timely execution of deliverables.
• Conduct financial and business analysis using business strategy frameworks.
• Interpret analytical results and generate insights and recommendations.
• Manage and deliver board-level and public-facing strategy documents, including quarterly board reports and annual report MD&A.
• Support Sun Life Canada's strategic priorities, including digital initiatives and operational efficiencies through AI technologies.
• Prepare and deliver formal presentations and informal updates for senior management.
• Present results, engage partners in next-step discussions, and support implementation of recommendations

Skills

Quantitative Analysis

Qualitative Analysis

Financial Modelling

Stakeholder Management

Problem Structuring

Excel Proficiency

PowerPoint Proficiency

Report Preparation

Presentation Skills

Research Skills

Communication Skills

Interpersonal Skills

Organization Skills

Collaboration Skills

Attention to Detail

Microsoft Office

Education

University degree in business administration, finance, economics, engineering, or related discipline

Tools

Excel

PowerPoint

Word

Microsoft Office

Job description

• Conduct quantitative and qualitative research and analysis independently
• Prepare and deliver recommendations on priority strategic questions for the Canadian Business
• Develop and syndicate board and public-facing strategy documents
• Engage executive stakeholders
• Collaborate with strategy team members and partners across the business
• Support delivery of strategic projects through workstream management, problem definition and structuring, cross-functional collaboration, updates, and timely execution of deliverables
• Conduct financial and business analysis using business strategy frameworks
• Interpret analytical results and generate insights and recommendations
• Manage and deliver board-level and public-facing strategy documents, including quarterly board reports and annual report MD&A
• Support Sun Life Canada's strategic priorities, including digital initiatives and operational efficiencies through AI technologies
• Prepare and deliver formal presentations and informal updates for senior management
• Present results, engage partners in next-step discussions, and support implementation of recommendations

Requirements

• Minimum 4 years of relevant business experience
• University degree in business administration, finance, economics, engineering, or related discipline
• Experience in management consulting, corporate strategy, a startup, as a Chief of Staff, or an equivalent role
• Experience managing and collaborating directly with very senior stakeholder groups, including C-Suite and Senior Vice Presidents
• Strong conceptual problem-solving skills, including structuring business problems, formulating and testing hypotheses, and developing recommendations
• Strong analytical skills and proficiency in financial modelling tools and techniques, especially Excel
• Ability to conduct quantitative and qualitative analysis and interpret and synthesize results
• Experience conducting in-depth secondary research; primary research experience is an asset
• Excellent oral and written communication and presentation skills
• Ability to prepare formal business reports and presentations using PowerPoint
• Strong interpersonal and stakeholder management skills
• Strong project management skills and ability to prioritize and organize work effectively under tight timelines
• High attention to detail
• Strong, preferably expert, knowledge of Microsoft Office products including Excel, PowerPoint, and Word
• Experience in insurance, health, wealth, or financial services is a plus but not required
• Experience in digital strategy and transformation is an asset
• Bilingualism in French and English, oral and written, is required for Quebec only

Core Competencies

Demonstrates strong analytical and problem-solving capabilities, with expertise in financial modeling and business strategy frameworks. Proficient in preparing and delivering strategic documents and presentations for senior stakeholders, while effectively managing cross-functional collaboration and project execution.

Highest-signal resume keywords

• Financial Modelling
• Business Strategy Frameworks
• Stakeholder ManagementProject Management
• Bilingualism in French and English

ATS Optimization Keywords

Hard Skills

• Quantitative Analysis
• Qualitative Analysis
• Business Analysis
• Presentation Skills
• Research Skills
• Excel Proficiency
• PowerPoint Proficiency
• Report Preparation
• Problem Structuring
• Strategic Recommendations

Soft Skills

• Interpersonal Skills
• Communication Skills
• Collaboration Skills
• Attention to Detail
• Organizational Skills

Industry Keywords

• Management Consulting
• Corporate Strategy
• Digital Strategy
• Insurance
• Financial Services
• Health
• Wealth

Tools & Technologies

• Microsoft Office
• Excel
• PowerPoint
• Word