Director, Direct Venture Pricing

Wawanesa; Winnipeg; Hybrid; CAD 170,000 - 220,000; Full time

Job summary

The Wawanesa Mutual Insurance Company seeks a Director, Direct Venture Pricing to lead pricing strategy for the Direct-to-Member portfolio within a hybrid Canadian setting. You will shape pricing governance, analytics, and profitability across diverse products and work with internal stakeholders in Canada.

In a start-up style environment, the role advances pricing sophistication using AI, predictive analytics and ML, and builds a high-performing pricing team.

Qualifications

• Minimum 10 years of insurance pricing experience across multiple lines of business, including at least three years in leadership.
• Start-up, advanced analytics, non-insurance pricing, or Life insurance experience is an asset.

Responsibilities

• Own D2M portfolio financial performance across insurance and non-insurance products by setting and executing pricing strategy, roadmap, and rate actions aligned with the business plan and market conditions.
• Lead advanced pricing models and methodologies using AI, predictive analytics, machine learning, and emerging data; incorporate cross-sell, bundling, and cross-subsidization across the product suite.
• Establish pricing-model governance, including validation, monitoring, documentation, compliance, risk management, and performance oversight.
• Partner with Product, Underwriting, Finance, Marketing, Claims, Technology, Data & Analytics and collaborate with other Business Lines as needed, to embed pricing insights in decisions and optimize portfolio performance.
• Monitor portfolio results, member research, market and competitor activity, regulation, and industry trends; identify risks and opportunities and recommend timely action.
• Develop pricing proposals and business cases supported by rigorous analysis; ensure pricing changes comply with provincial and federal insurance requirements.
• Advise and influence senior leaders, facilitate cross-functional alignment, and lead strategic pricing initiatives from concept through implementation and benefits realization.
• Build and lead a high-performing pricing team through talent attraction, coaching, development, and retention; foster innovation, accountability, technical excellence, collaboration, continuous learning, and profitable growth.

Job description

Select how often (in days) to receive an alert:

Job ID:10284

Employment Type: New Role

Work Environment: 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; Quebec City, QC, Moncton, NB; Dartmouth; NS.

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: $170,000- $220,000. Candidates with salary expectations outside of the range are still encouraged to apply.

About The Wawanesa Mutual Insurance Company
Founded in 1896, The Wawanesa Mutual Insurance Company is one of Canada’s largest mutual insurers, 100% owned by its members, with more than $4.1 billion in annual revenue and $12.5 billion in assets. Headquartered in Winnipeg, Wawanesa is the parent company of Wawanesa Life, which provides life insurance solutions throughout Canada, and Western Financial Group, a leading national distributor of personal and business insurance. In March of 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 proudly serves more than 1.8 million members and we are home to more than 3,000 employees across Canada. The company actively gives back to organizations that strengthen communities, donating more than $4 million annually to charitable organizations, including more than $2 million each year in support of people on the front lines of climate change. Learn more at 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

The Director, Direct Venture Pricing leads the Direct-to-Member (D2M) pricing strategy and builds a pricing capability that supports sustainable profitability, competitive positioning, and member value. In a start-up environment, the role advances sophisticated pricing, analytics, and modeling practices for a direct-digital, AI-native business.

Partnering across Product, Underwriting, Claims, Marketing, Data Science, Technology, Finance, Regulatory Affairs and other Business Lines, the Director owns technical pricing, segmentation, rate-level management, and pricing frameworks. The role advises senior leaders and balances profitability, member outcomes, regulation, and business objectives across the product portfolio.

Job Responsibilities

• Own D2M portfolio financial performance across insurance and non-insurance products by setting and executing pricing strategy, roadmap, and rate actions aligned with the business plan and market conditions.
• Lead advanced pricing models and methodologies using AI, predictive analytics, machine learning, and emerging data; incorporate cross-sell, bundling, and cross-subsidization across the product suite.
• Establish pricing-model governance, including validation, monitoring, documentation, compliance, risk management, and performance oversight.
• Partner with Product, Underwriting, Finance, Marketing, Claims, Technology, Data & Analytics and collaborate with other Business Lines as needed, to embed pricing insights in decisions and optimize portfolio performance.
• Monitor portfolio results, member research, market and competitor activity, regulation, and industry trends; identify risks and opportunities and recommend timely action.
• Develop pricing proposals and business cases supported by rigorous analysis; ensure pricing changes comply with provincial and federal insurance requirements.
• Advise and influence senior leaders, facilitate cross-functional alignment, and lead strategic pricing initiatives from concept through implementation and benefits realization.
• Build and lead a high-performing pricing team through talent attraction, coaching, development, and retention; foster innovation, accountability, technical excellence, collaboration, continuous learning, and profitable growth.

Qualifications

• Minimum 10 years of insurance pricing experience across multiple lines of business, including at least three years in leadership. Start-up, advanced analytics, non-insurance pricing, or Life insurance experience is an asset.
• Under