Director, Personal Lines - Market Segment Leaders

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Date: Oct 9, 2025

Location: Hybrid - Canada, CA Montreal, QC (Hybrid), CA Kitchener, ON (Hybrid), CA Dartmouth, NS (Hybrid), CA North York - Toronto, ON (Hybr, CA Edmonton, AB (Hybrid), CA Calgary, AB (Hybrid), CA Vancouver, BC (Hybrid), CA Winnipeg, MB (Hybrid), CA

Company: Wawanesa Insurance

Job ID: 9513 


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: $150,000- $200,000. Candidates with salary expectations outside of the range are still encouraged to apply. 

 


About Us
At Wawanesa, we’re proud to 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, ON; Kitchener, ON; Ottawa, ON; Montreal, QC; Moncton, NB; Dartmouth; NS 
 

The Wawanesa Mutual Insurance Company (“Wawanesa Mutual”), founded in 1896, is one of Canada’s largest mutual insurers, with over $3.5 billion in annual revenue and assets of $10 billion (CAD). Wawanesa Mutual, with its National Headquarters in Winnipeg, is the parent company of Wawanesa Life, which provides life insurance products and services throughout Canada, and Western Financial Group, which distributes personal and business insurance across Canada. Wawanesa proudly serves more than 1.7 million members in Canada, and we are home to more than 3,600 employees distributed across the Canadian regions and communities where we operate. We give back to organizations that strengthen communities, donating more than $3.5 million annually to charitable organizations, including over $2 million annually in support of people on the front lines of climate change. To learn more visit 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, Personal Lines - Market Segment Leaders, reports to the Vice President, Personal Lines, Product Management. This role carries delegated accountability for portfolio performance, including profit, loss, and growth of all personal insurance products on a national basis. The Director ensures alignment with Wawanesa’s mutual purpose and long-term business goals while influencing and collaborating on strategies and tactics across the organization to deliver on the Personal Lines (PL) annual budgetary objectives.


This position requires strong strategic and partnership capabilities, working directly with leaders across the business to optimize performance, identify growth opportunities, prioritize initiatives that impact financial results, and drive execution in collaboration with key stakeholders and functions.

Job Responsibilities

  • Collaborate with senior leaders to develop strategies & provide direction that drives the execution of annual financial objectives.
  • Provide comprehensive oversight of the business, identifying issues & opportunities, developing plans and strategies to achieve objectives while influencing & collaborating with enabling functions to deliver optimal outcomes.
  • Build strong, trust-based relationships with colleagues & foster continuous engagement with stakeholders
  • Partner with sales/distribution on broker strategies & execute growth tactics.
  • Develop and deliver go-to-market strategies & messaging in collaboration with sales/distribution and marketing/communications, ensuring clarity & alignment for brokers and members when product or pricing changes occur.
  • Drive portfolio optimization by balancing growth, profitability, & risk while ensuring products remain competitive and aligned with member needs.
  • Champion product innovation by identifying new opportunities, piloting enhancements, & guiding the development of solutions that differentiate Wawanesa in the marketplace.
  • Ensure compliance with regulatory requirements across all jurisdictions, collaborating with legal and compliance functions to proactively address emerging issues.
  • Monitor and evaluate product and underwriting performance, along with the broader financial performance.
  • Assess emerging risks and market dynamics to inform business decisions and continuous improvement; adjust strategies to mitigate risk based on industry, economic, & legislative developments.
  • Identify root causes of results & performance variances, implementing initiatives to achieve or exceed budgetary targets.
  • Represent Wawanesa externally with industry groups, regulators, and broker partners to advance Wawanesa’s reputation and influence in the personal insurance market.

Qualifications

  • Bachelor’s degree in business, insurance, or a related field. MBA or relevant professional designation (i.e. FCIP, CIP) considered an asset.
  • Minimum 7 years of progressive leadership experience in the Canadian P&C insurance industry, with considerable experience in product management, underwriting strategy, and portfolio oversight.
  • Proven success leading teams and driving cross-functional collaboration within a matrixed organization.
  • Strong technical expertise in pricing, product, underwriting, and actuarial practices, with exceptional quantitative and analytical skills.
  • Demonstrated financial acumen with experience managing P&L and strong knowledge of reinsurance products and processes.
  • Critical thinker who leverages data and scenario analysis to inform decision-making; decisive and accountable with the ability to prioritize effectively.
  • Persuasive and influential leader, able to motivate others and drive success without relying solely on direct reporting relationships.
  • Deep understanding of Canadian personal insurance markets, regulatory environments, emerging risks, and evolving member needs.
  • Strong alignment with Wawanesa’s mutual values of integrity, service, innovation, and a commitment to looking after one another.
  • Bilingualism in English and French considered an asset.
     


Wawanesa is proud to be one of Manitoba’s Top Employers, a Kincentric Best Employer in Canada and a Forbes Best Employer in Canada recognizing an exceptional place to work!


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 jobs@wawanesa.com.
 

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