Manager, Strategy Planning

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Date: Feb 25, 2026

Location: North York - Toronto, ON (Hybr, CA Ottawa, ON (Hybrid), CA Calgary, AB (Hybrid), CA Edmonton, AB (Hybrid), CA Kitchener, ON (Hybrid), CA Dartmouth, NS (Hybrid), CA Montreal, QC (Hybrid), CA Winnipeg, MB (Hybrid), CA Vancouver, BC (Hybrid), CA Moncton, NB (Hybrid), CA

Company: Wawanesa Insurance

 

Job ID: 9821 


Employment Type: New Role

Working Business Language: English. This role is considered a head-office role and will be required to communicate with internal stakeholders across Canada where the primary business language utilized is English.
 

Salary: At Wawanesa, salary is only one component of a holistic, comprehensive and competitive offering that we provide to our employees. In addition to salary, full-time and part-time permanent employees are eligible for an annual bonus plan, leave of absence top-up programs and provided with generous vacation time, personal days, premium free benefits and pension plan. 
 

The salary offered for this role is determined with consideration to various factors, including but not limited to: your work location, local labour market conditions, external market salary data, internal pay equity and the knowledge, skills, experience and anticipated proficiency in the role. The salary offered is estimated to be within the following range: $115,000 - $155,000. Candidates with salary expectations outside of the range are still encouraged to apply.

 

About Us
At Wawanesa, we offer a hybrid work environment that offers flexibility to our employees in balancing in-office (2 days per week OR 15 hours per week in a Wawanesa office) and remote work. You may work from any of the following locations: Winnipeg, MB; Vancouver, BC; Calgary, AB; Edmonton, AB; Toronto (North York), ON; Kitchener, ON; Ottawa, ON; Montreal, QC; Moncton, NB; Dartmouth; NS. 
 

The Wawanesa Mutual Insurance Company (“Wawanesa Mutual”), founded in 1896, is one of Canada’s largest mutual insurers, with over $3.5 billion in annual revenue and assets of $10 billion (CAD). Wawanesa Mutual, with its National Headquarters in Winnipeg, is the parent company of Wawanesa Life, which provides life insurance products and services throughout Canada, and Western Financial Group, which distributes personal and business insurance across Canada. Wawanesa proudly serves more than 1.7 million members in Canada, and we are home to more than 3,300 employees distributed across the Canadian regions and communities where we operate. We give back to organizations that strengthen communities, donating more than $3.5 million annually to charitable organizations, including over $2 million annually in support of people on the front lines of climate change. We are also proud to be recognized as one of Manitoba’s Top Employers. To learn more visit wawanesa.com. 


We are currently looking for dedicated, driven, and enthusiastic individuals who thrive in an environment that welcomes change and are looking for an opportunity for diverse experience and advancement on a growing team.
 

Job Overview

As part of Wawanesa’s Strategy & Innovation team, the Manager, Strategy Planning works collaboratively with stakeholders across the organization to guide bold strategic choices, monitor our progress toward shared aspirations, and advance enterprise alignment through forward-looking insights. 

 

Working under minimal supervision, you will lead and support a broad spectrum of enterprise strategy planning activities, from supporting annual and multiyear strategy cycles, to synthesizing insights and trends, assessing progress through KPIs, and developing actionable recommendations that strengthen Wawanesa’s resilience and long-term competitiveness. You will leverage your passion for strategy, systems thinking, and structured problem solving to lead cross-functional teams, influence senior leaders, and translate complex information into clear strategic narratives - connecting enterprise aspirations to coordinated plans that enable effective decision-making and execution. Your leadership ensures Wawanesa’s strategies remain robust, responsive, and grounded in a deep understanding of our operating landscape. 

Job Responsibilities 

  • Lead the development of strategic insights that integrate internal data, industry trends and market activities; working to stress test strategic decisions and assumptions, ensuring alignment of our choices with market demands and member needs. 
  • Lead the development of clear and compelling enterprise strategy reporting, including KPI tracking, progress assessments, hypotheses tracking, and insights on strategic risks and opportunities. 
  • Oversee the creation and delivery of strategic market and competitive intelligence reporting, proactively identifying and contextualizing inflection points, emerging risks, and opportunities that inform strategic adjustments and build competitive advantage. 
  • Collaboratively manage strategic problem-solving and scenario-planning work efforts in partnership with executive sponsors and stakeholders across the enterprise, leveraging structured methodologies and tools (i.e., Strategy Process Map, Value Proposition Canvas, etc.). 
  • Support the planning, coordination, and facilitation of Wawanesa’s enterprise strategy cycle in collaboration with the Executive Leadership Team, ensuring alignment with our purpose, vision, and strategic aspirations. 
  • Lead, coach, and develop a team of internal consultants and strategy professionals, fostering a culture of curiosity, teamwork, and high performance where employees meet their full potential. 
  • Act as a subject matter expert on our strategy process and tools, passionately advocating for the advancement of our strategy, strategic thinking and problem solving.  

Qualifications

  • Minimum five years’ combined experience in strategy development, business analysis or related roles, with increasing leadership responsibilities and progressive experience in insurance, financial services, or an equivalent business environment. 
  • Post-secondary degree in Business or related discipline; a graduate degree (MBA or equivalent) is considered an asset. 
  • Demonstrated experience delivering corporate strategic initiatives or projects leveraging frameworks, methodologies and structured problem solving (i.e. Playing to Win, Strategy Process Map, OGSM, etc). 
  • Advanced knowledge of insurance financials and demonstrated ability to lead financial analysis; Expertise working in financial services, with MSA Research, or insurance industry accreditations considered an asset. 
  • Demonstrated ability to lead, coach and develop high-performing teams, build effective relationships, and manage execution and change to execute shared goals. 
  • Strong systems thinking and analytical skills, with the ability to synthesize complex qualitative and quantitative information into clear strategic insights and implications and communicate them effectively to executive audiences. 
  • Strong facilitation and presentation skills, with experience in designing and leading workshops and collaborative working groups that explore the future, generate insight, foster alignment, and enable informed decision making. 
  • Proficient with Microsoft Office Suite, particularly Excel and PowerPoint; Experience and experimentation with CoPilot or equivalent tools to enhance team productivity considered an asset.

 

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Diversity Equity, Inclusion & Belonging

At Wawanesa, we are committed to Diversity, Equity, Inclusion and Belonging (DEIB) and believe that our strength lies in the diversity of our people – this is supported by having a representative workforce.

We welcome applications from all qualified candidates, including racialized persons, women, Indigenous Peoples, persons with disabilities, members of the 2SLGBTQIA+ community, gender-diverse and neurodiverse individuals, and anyone who can contribute to the further diversification of thought and ideas. 
 

We aim to ensure our recruitment process is accessible to all candidates. If you require accommodations during any stage of the recruitment process, please reach out in confidence to jobs@wawanesa.com.
 

All Wawanesa job applicants are subject to Wawanesa's Privacy Policy.

Please note that the recruitment process for this position may involve the use of AI tools to screen, assess, or select applicants. All final decisions are taken or reviewed by human recruiters and human hiring leaders in compliance with all applicable legislation.