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Senior Underwriting Training Specialist - Commercial Lines

Remote / Online - Candidates ideally in
Edmonton, Alberta, P5J, Canada
Listing for: Wawanesa
Full Time, Part Time, Remote/Work from Home position
Listed on 2026-08-31
Job specializations:
  • Insurance
    Insurance Analyst, Underwriter
Salary/Wage Range or Industry Benchmark: 95000 - 120000 CAD Yearly CAD 95000.00 120000.00 YEAR
Job Description & How to Apply Below

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Location: Hybrid
- Canada, CA Kitchener, ON (Hybrid), CA Ottawa, ON (Hybrid), CA Lethbridge, AB (Hybrid), CA Edmonton, AB (Hybrid), CA Dartmouth, NS (Hybrid), CA Montreal, QC (Hybrid), CA Thunder Bay, ON (Hybrid), CA Lloydminster, AB (Hybrid), CA Calgary, AB (Hybrid), CA Winnipeg, MB (Hybrid), CA Wawanesa, MB (Hybrid), CA Vancouver, BC (Hybrid), CA Moncton, NB (Hybrid), CA North York
- Toronto, ON (Hy , CA

Job :10015

Employment Type: New Role

Working Business Language :
English. This role is considered a head-office role and will be required to communicate with internal and external stakeholders across Canada where the primary business language for this role is English. As such, the successful candidate must be fully proficient in 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: $95,000 - $120,000. Candidates with salary expectations outside of the range are still encouraged to apply.

About Us At Wawanesa, 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;
Wawanesa, MB;
Vancouver, BC;
Calgary, AB;
Edmonton, AB;
Lethbridge, AB;
Toronto (North York), ON;
Kitchener, ON;
Ottawa, ON;
Montreal, QC;
Quebec City, 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 3,300 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.

We are also proud to be recognized as one of Manitoba’s Top Employers. To learn more visit

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

Working under minimal supervision, the Senior Underwriting Training Specialist is a pivotal role in the creation, maintenance, and utilization of an underwriting training program for Commercial Lines. The successful candidate will support the effectiveness and execution of underwriting strategy and acts as a critical bridge between underwriting, operations, and enterprise stakeholders.

Job Responsibilities

  • Lead the design, development, and implementation of underwriting learning experiences for Commercial Lines, determining how best to scale programming, ensuring to choose appropriate training methods to best support Commercial teams.
  • Create clear and consistent, audience-appropriate underwriting communications related to these training experiences, ensuring that complex concepts are translated to practical, easy-to-use tools.
  • Develop and maintain underwriting training roadmaps, conducting…
Position Requirements
10+ Years work experience
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