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About the Role

The Strategic Pricing Initiatives Director leads direct-to-member (DTM) pricing strategy and develops pricing capabilities to drive long-term profitability, competitive positioning, and member value. In an emerging enterprise environment, this role develops sophisticated pricing, analytics, and modeling practices for digital companies leveraging AI. Collaborating with Product, Underwriting, Claims, Marketing, Data Science, Technology, Finance, Regulatory Affairs, and other business units, the Director is accountable for technical pricing, segmentation, rate management, and pricing frameworks. The role advises senior leadership, balancing profitability, member outcomes, regulatory, and business objectives across the portfolio.

Responsibilities

Ensure financial performance of the DTM portfolio across related and unrelated insurance products by developing and implementing a pricing strategy, roadmap, and pricing metrics per the business plan and market conditions.
Lead advanced pricing methodologies and models using AI, predictive analytics, machine learning, and emerging data. Integrate cross-selling, bundling, and co-insurance across the product suite.
Develop pricing model governance, including validation, monitoring, documentation, compliance, risk management, and performance tracking.
Collaborate with Product, Underwriting, Finance, Marketing, Claims, Technology, Data & Analytics, and other business units as needed to incorporate pricing insights into decision-making and optimize portfolio performance.
Monitor portfolio results, member research, market and competitor activities, regulation, and industry trends. Identify timely risks and opportunities and recommend timely actions.
Develop pricing proposals and business cases supported by rigorous analysis. Ensure pricing changes comply with provincial and federal insurance requirements.
Advise and influence senior leadership, facilitate cross-functional alignment, and lead strategic pricing initiatives from ideation through implementation to benefit realization.
Develop and lead a high-performing pricing team by attracting, training, developing, and retaining talent. Foster innovation, accountability, technical excellence, collaboration, continuous learning, and profitable growth.

Requirements

At least 10 years of insurance pricing experience across multiple industry sectors, including at least 3 years in a management role.
Experience in emerging enterprise, advanced analytics, non-insurance pricing, or life insurance is an asset.
In-depth expertise in P&C insurance products, pricing, underwriting, insurance operations, regulation, advanced statistical modeling, AI, predictive analytics, and model governance.
Strong business acumen, analytical judgment, and problem-solving skills; ability to target critical issues, make informed decisions under pressure, and translate analysis into action.
Proven ability to lead strategy and transformation, influence complex decisions, build credibility and relationships with stakeholders, and communicate effectively in writing, presentations, and discussions.
Intrapreneurial and innovative; resilient, adaptable, and strategic-minded; comfortable in a fast-paced environment; communicates a compelling vision, proactively identifies opportunities, and drives measurable results.

Skills

AI
Predictive analytics
Machine learning
Advanced statistical modeling

Location

Winnipeg, MB
Vancouver, BC
Calgary, AB
Edmonton, AB
Toronto (North York), ON
Kitchener, ON
Ottawa, ON
Montréal, QC
Ville de Québec, QC
Moncton, NB
Dartmouth, NS

Work Type

Hybrid

Experience Level

10+ years
3+ years management experience

Education Level

Undergraduate degree in Actuarial Mathematics, Statistics, Mathematics, Business, Economics, or a related field.
ACAS, FCAS or equivalent actuarial designation is a significant asset.
MBA, CPA, FCPA or other relevant designation is an asset.

Salary/Compensations

$170,000 - $220,000

Benefits

Annual incentive program
Supplementary leave program
Generous vacation days
Personal days
Non-premium benefits
Pension plan

About the Company

Founded in 1896, The Wawanesa Mutual Insurance Company is one of Canada's largest mutual insurance companies, wholly owned by its members, with over $4.1 billion in annual revenue and $12.5 billion in assets.
Wawanesa, headquartered in Winnipeg, is the parent company of Wawanesa Life, which provides life insurance solutions across Canada, and Western Financial Group, a major national distributor of personal and business insurance.
In March 2026, Wawanesa entered into an agreement to acquire Everest Insurance Company of Canada to strengthen its commercial insurance capabilities and advance its long-term growth strategy.
Wawanesa is proud to serve over 1.8 million members and employs over 3,000 people across Canada.
The company actively gives back to organizations that strengthen communities, donating over $4 million annually to charities, including over $2 million annually to support those on the front lines helping communities adapt to climate change.
Learn more at wawanesa.com.

Equal Opportunity

At Wawanesa, we are committed to Diversity, Equity, Inclusion, and Belonging (DEIB), and we believe our strength lies in the diversity of our people, resulting in a workforce representative of the entire population.
We encourage all qualified candidates to apply, whether they are racialized people, women, Indigenous people, persons with disabilities, members of the 2ELGBTQIA+ community, people of diverse gender identities, and neurodiverse individuals, or anyone who can contribute to greater diversity of perspectives and ideas.
We want to ensure our recruitment process is accessible to all candidates. If you require accommodation during the recruitment process, you can confidently email jobs@wawanesa.com.
All applicants for employment at Wawanesa are subject to the applicable Employee Personal Information Policy.
Please note that as part of this recruitment process, AI tools may be used to screen, assess, or select applications. All final decisions are made after review by recruiters and hiring managers, in compliance with all applicable laws.