Director, Strategy & Transformation

Job Description

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This is a high-visibility strategy role supporting the SVP, Chief Experience, Digital and AI Officer and Chief Information Officer and the broader leadership team on high-priority questions facing the organization. Reporting to the AVP, Business Insights & Strategic Execution, a strategic and execution partner to the SVP, the Director will work across AI, digital, client experience and technology to frame complex problems, generate insights, develop executive recommendations and help mobilize priority initiatives.

The role offers broad exposure across some of Sunlife Canada’s most important transformation priorities and the opportunity to work closely with senior leaders on issues ranging from emerging AI opportunities and digital and client priorities to strategic investments, organizational effectiveness and transformation. The successful candidate will bring rigorous, hypothesis-driven problem solving, strong business and financial judgment, and exceptional executive communication skills.

Deep technology expertise is not required. We are looking for an exceptional strategist and problem solver who is intellectually curious about AI, digital and technology and able to build fluency quickly.

What will you do?

• Strategic problem solving: lead high-priority strategic assignments from problem definition through recommendation and mobilization, structuring ambiguous questions, developing the fact base, evaluating alternatives and helping leadership translate decisions into action.
• Analysis and insight: apply consulting-style problem solving, including hypothesis development, market and competitive analysis, benchmarking, financial modeling, scenario analysis and synthesis of internal and external perspectives.
• Executive decision support and storytelling: develop crisp, answer-first executive narratives and decision materials that turn complex analysis into clear choices, recommendations, trade-offs and implications.
• Cross-functional alignment: partner with leaders across business, technology, finance, risk, data, digital and corporate functions to test perspectives, build alignment and advance priority initiatives.
• Mobilization and execution support: translate strategic recommendations into actionable plans, including sequencing, dependencies, measures of success, accountabilities and key executive decisions.
• Project leadership: independently manage high-priority assignments or strategic initiatives and provide day-to-day leadership to cross-functional teams contributing to the work, where needed.

What do you need to succeed?

Education & Experience

• 5+ years of relevant professional experience, ideally spanning management consulting, corporate strategy, and/or strategic planning.
• Management consulting or comparable strategy experience is strongly preferred, with demonstrated strength in hypothesis-driven problem solving, qualitative and quantitative analysis, and executive communication.
• University degree in business, economics, engineering, or another relevant discipline; an MBA or other relevant graduate degree is an asset.
• Demonstrated experience independently structuring ambiguous problems, conducting rigorous qualitative and quantitative analysis, and translating findings into actionable recommendations to senior executives.
• Experience with AI, digital, client experience, technology or business transformation is an asset.
• Demonstrated experience working across functions, navigating organizational complexity and influencing stakeholders.
• Experience in financial services or another large, matrixed organization is preferred.

Skills & Competencies

• Exceptional executive communication and storytelling skills, including the ability to develop concise, answer-first presentations and written recommendations.
• Strong business and financial acumen, with the ability to evaluate strategic choices, benefits, costs, risks and trade-offs.
• Strong judgment, intellectual curiosity and comfort operating in ambiguous, fast-moving and highly visible situations.
• Ability to work effectively with senior executives and build alignment across stakeholders with different perspectives and priorities.
• Advanced PowerPoint and Excel capabilities, including experience developing executive-level presentations and analytical models. Experience with other analytical tools or dashboards is an asset.
• Intellectual curiosity and sufficient fluency in AI, digital and technology topics to engage credibly with subject-matter experts and connect emerging capabilities to business outcomes.

What’s in it for you?

• A competitive salary and bonus program, based on market scale
• Being part of our journey in developing the next greatest digital experience
• A flexible group insurance program starting on your first day of work to meet your needs and those of your family
• Our Share Ownership Program gives you the opportunity to invest in Sun Life while benefiting from employer matching contributions
• Our unique Sabbatical Program gives you the opportunity to take up to 6 weeks off, every five years.
• We are proud to be on the 2026 Best Workplaces in Canada list by Great Place to Work.