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About the Role

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.

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.

Requirements

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.
Undergraduate degree in Actuarial Mathematics, Statistics, Mathematics, Commerce, Economics, or a related field.
ACAS, FCAS, or equivalent actuarial designation strongly preferred; MBA, CIP, FCIP, or another relevant designation is an asset.
Deep expertise in P&C products, pricing, underwriting, insurance operations, regulation, advanced statistical modeling, AI, predictive analytics, and model governance.
Strong business acumen, analytical judgment, and problem-solving; able to identify critical issues, make sound decisions under pressure, and translate analysis into action.
Proven ability to lead strategy and transformation, influence complex decisions, build credibility and stakeholder relationships, and communicate effectively in writing, presentations, and discussion.
Intrapreneurial and innovative; resilient, adaptable, and strategically 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
Montreal, QC
Quebec City, QC
Moncton, NB
Dartmouth, NS

Work Type

Hybrid
Full-time
Part-time

Experience Level

Leadership
10+ years of insurance pricing experience

Education Level

Undergraduate degree in Actuarial Mathematics, Statistics, Mathematics, Commerce, Economics, or a related field.
ACAS, FCAS, or equivalent actuarial designation
MBA
CIP
FCIP

Salary/Compensations

$170,000- $220,000

Benefits

Annual bonus plan
Leave of absence top-up programs
Generous vacation time
Personal days
Premium free benefits
Pension plan

About the 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.
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.

Equal Opportunity

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.