You'll work with dynamic colleagues
- experts in their fields
- who are eager to share their knowledge with you. Your leaders will inspire and help you reach your potential and soar to new heights. At Sun Life, we're driven by our Purpose: helping our Clients achieve lifetime financial security and live healthier lives. When you join Sun Life, you'll work with passionate colleagues and empowering leaders who support your growth and celebrate your contributions, so you can make a meaningful difference in our Clients' lives. Discover how you can make a difference in the lives of individuals, families and communities around the world.
This is a high-visibility strategy role supporting the SVP, Chief Experience, Digital and AI Officer & 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. 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.
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 explicit 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.
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.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. 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. Strong business and financial acumen, with the ability to evaluate strategic choices, benefits, costs, risks and trade-offs. 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.
A competitive salary and bonus program, based on market scaleBeing part of our journey in developing the next greatest digital experienceA flexible group insurance program starting on your first day of work to meet your needs and those of your familyOur Share Ownership Program gives you the opportunity to invest in Sun Life while benefiting from employer matching contributionsOur unique Sabbatical Program gives you the opportunity to take up to 6 weeks off, every five years.
In addition to Base Pay, eligible Sun Life employees participate in various incentive plans, payment under which is discretionary and subject to individual and company performance.
Diversity and inclusion have always been at the core of our values at Sun Life. A diverse workforce with wide perspectives and creative ideas benefits our Clients, the communities where we operate and all of us as colleagues. Persons with disabilities w

📌 Director, Strategy (Winnipeg)
🏢 Sun Life
📍 Winnipeg