Underwriting Technical Specialist - Commercial Lines-Auto

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Date: Oct 6, 2026

Location: North York - Toronto, ON (Hybr, CA Ottawa, ON (Hybrid), CA Kitchener, ON (Hybrid), CA Dartmouth, NS (Hybrid), CA Moncton, NB (Hybrid), CA

Company: Wawanesa Insurance

Job ID: 10344 


Employment Type: Existing 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: Toronto (North York), ON; Kitchener, ON; Ottawa, ON; Moncton, NB; Dartmouth; NS. 

 

Working Business Language: 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: $90,000 - $110,000. 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, fully owned by its more than 1.8 million members. Headquartered in Winnipeg, Wawanesa is the parent company of WSI™, a specialty insurer delivering tailored solutions built around unique needs; Wawanesa Life, a provider of life insurance products; and Western Financial Group, a leading national distributor of personal and commercial insurance.

Wawanesa is committed to helping communities thrive in a changing world. The company invests more than $4 million annually in charitable initiatives, including $2.5 million each year to support people and communities on the front lines of climate change. Learn more at wawanesa.com.

 

We are currently seeking dedicated, driven, and enthusiastic individuals who thrive in a dynamic environment, embrace change, and are eager to gain diverse experience while advancing their careers as part of a growing team.

Job Overview

Working under minimal supervision, the Underwriting Technical Specialist – Commercial Lines Auto, assists with both strategic and business as usual initiatives to achieve profitability, competitiveness and efficiency.

 

Job Responsibilities

  • Liaise with Executive Office, as a subject matter expert, to assist with (but not limited to):
    • Strategic Initiatives, including technological advancements.
    • Rate and Product Development.
    • Regulatory Changes and Reporting.
    • Company Benchmarks.
    • Portfolio analysis and strategy development.
    • Customer Engagement.
  • Perform research and analysis of the industry and company data to contribute towards assigned initiatives.
  • Champion the development and implementation of business change.
  • Maintain existing documentation so that it reflects up to date and proper information.
  • Provide technical assistance and training to ensure consistency in the implementation of change.
  • Mentor and develop team members and facilitate sessions for the sharing of knowledge and best practices.
  • Perform risk analysis using technology as well as external data sources for the purposes of quoting, negotiating and authorizing the acceptance of risk.  
  • Lead and/or participate in periodic work reviews for quality assurance purposes.
  • Foster positive working relationships with internal and external parties, including other regional offices and networking at industry events.
  • Perform other duties as assigned.

Qualifications

  • Seven years Commercial Auto industry experience.
  • Post-secondary education or related business experience.
  • Completed a Property and Casualty Industry Designation.
  • Working knowledge of Microsoft Office Suite.
  • Excellent attention to detail with the ability to review information carefully and comprehensively.
  • Excellent analytical, and problem solving with the ability to select and implement best solutions.
  • Excellent decision making skills with the ability to provide justification.
  • Excellent customer service skills.
  • Expert communication skills with the ability to present information in a convincing manner.
  • Strong leadership skills to positively influence team members and provide direction.
  • Strong ability to multi-task and monitor progress to meet deadlines.
  • Ability and willingness to travel.


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.
 

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.