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Job Opportunities Director, Direct Venture Pricing

Wawanesa Insurance


Job Location:

Toronto - Canada

Monthly Salary: $ 170000 - 220000
Posted: 30 August 2026 (30+ days ago)
Application Deadline: 27 November 2026
Vacancies: 1 Vacancy

Job Summary

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 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 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: $170000- $ 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 Canadas 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 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 3000 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 .

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 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.
  • 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.


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 .

All Wawanesa job applicants are subject to Wawanesas .

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.


Required Experience:

Director


About Company

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Wawanesa Insurance offers affordable rates for homeowners, home, renters, car insurance and more in the U.S. Get a free insurance quote online to see how much you can start saving!

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