Director, Strategy & Transformation

Sun Life; Toronto; Hybrid; CAD 130,000 - 180,000; Full time

Benefits offered by this job

Bonus program

Flexible group insurance

Share Ownership Program

Sabbatical program (6 weeks every 5)**

Hybrid work model

Best Workplaces Canada

Job summary

Sun Life in Canada is seeking a senior strategy leader to partner with the SVP and leadership team on high-priority questions spanning AI, digital, client experience and technology. The Director will frame problems, generate insights and craft executive recommendations to mobilize priority initiatives.

The role requires hypothesis-driven analysis, strong business and financial judgment, and exceptional communication with senior executives.

Qualifications

• 5+ years in strategy, consulting or corporate strategy roles.

Responsibilities

• Lead high-priority strategic assignments from problem definition through recommendations and mobilization.
• Develop executive narratives and decision materials for senior leadership.
• Collaborate with cross-functional partners across AI, digital, client experience, finance and technology.
• Translate strategic recommendations into actionable plans with clear milestones.

Skills

Executive communication

Strategic thinking

Financial modeling

Presentation skills

Problem solving

AI & digital fluency

Education

MBA or related graduate degree

Bachelor's degree in business, economics, engineering or related

Tools

PowerPoint

Excel

Dashboards/Analytics tools

Job description

You are as unique as your background, experience and point of view. Here, you’ll be encouraged, empowered and challenged to be your best self. 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. Every day, you’ll have new and exciting opportunities to make life brighter for our Clients - who are at the heart of everything we do. At Sun Life, we're driven by our Purpose: helping our Clients achieve lifetime financial security and live healthier lives. Our values shape how we work: caring, authentic, bold, inspiring, and impactful. 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.

Job Description

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. 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.

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.
• The Base Pay range is for the primary location for which the job is posted. It may vary depending on the work location of the successful candidate or other factors.
• 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.
• Certain sales focused roles have sales incentive plans based on individual or group sales results.

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. We welcome applications from qualified individuals from all backgrounds.

Persons with disabilities who need accommodation in the application process, or those needing job postings in an alternative format, may e-mail a request to [e-mail].

We are proud to be a hybrid organization that offers our employees the choice and flexibility to work from both the office and virtually based on the needs of the business, our Clients and you.

We may use artificial intelligence to support candidate sourcing, screening, interview scheduling.

We thank all applicants for showing an interest in this position. Only those selected for an interview will be contacted.

Salary Range: 130,000/130 000 - 180,000/180 000

Job Category: Business Development - Non Actuarial

Posting End Date: 19/11/2026

Shine together At Sunlife, you can be your most brilliant self. Our supportive, flexible, and inclusive work environment is one where you – and your career – can thrive. Whatever your aspirations, collaborative leaders and colleagues are ready to help you learn, grow, and succeed. Make life brighter We’re a global company with a passion for people. Our purpose is to help Clients build lifetime financial security and lead healthier lives. As part of Sunlife’s growing team, you have an impact on people in your community and around the world. There’s power in numbers. As part of Sunlife’s growing team, you have an impact on people in your community and around the world.

Shape the future With an optimistic eye

Join us. Together, we can make the future brighter. Join a top employer for a brighter future. Visit Sunlife Careers