Manager, Strategy Planning

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 are provided with generous vacation time, personal days, premium free benefits and a 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.

Hybrid Work Environment: 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 company offers flexibility with 2 days per week or 15 hours per week in a Wawanesa office, or remote work.

About Wawanesa: Founded in 1896, Wawanesa Mutual Insurance Company is one of Canada’s largest mutual insurers, with over $3.5 billion in annual revenue and assets of $10 billion (CAD). The company is the parent of Wawanesa Life and Western Financial Group, serving more than 1.7 million members across Canada and employing over 3,300 people. Wawanesa is recognized as one of Manitoba’s Top Employers and supports community initiatives with more than $3.5 million donated annually.

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 progress toward shared aspirations, and advance enterprise alignment through forward‑looking insights. Working under minimal supervision, you will lead 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.

• Lead the development of strategic insights that integrate internal data, industry trends and market activities; work to stress test strategic decisions and assumptions, ensuring alignment with market demands and member needs.
• Lead the development of clear and compelling enterprise strategy reporting, including KPI tracking, progress assessments, hypothesis 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 (e.g., Strategy Process Map, Value Proposition Canvas).
• 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 reach their full potential.
• Act as a subject‑matter expert on our strategy process and tools, passionately advocating for the advancement of strategy, strategic thinking and problem solving.

• Minimum five years’ combined experience in strategy development, business…