Instructional Designer - Commercial Lines
Date: Apr 7, 2026
Location: Winnipeg, MB (Hybrid), CA Vancouver, BC (Hybrid), CA Hybrid - Canada, CA Edmonton, AB (Hybrid), CA Calgary, AB (Hybrid), CA North York - Toronto, ON (Hybr, CA Moncton, NB (Hybrid), CA Kitchener, ON (Hybrid), CA Montreal, QC (Hybrid), CA Dartmouth, NS (Hybrid), CA
Company: Wawanesa Insurance
Job ID: 9950
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: $75,000 - $95,000. 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 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 Instructional Designer plays a critical role in enhancing underwriting capability across Commercial Lines by designing, developing, and delivering high quality learning experiences. This role collaborates closely with enterprise-level subject matter experts (SMEs), Learning & Development partners, and business leaders to build programming and translate complex technical intelligence that elevates technical proficiency, strengthen judgment-based decision making, and reinforces underwriting excellence.
Job Responsibilities
- Partner with underwriting leaders, SMEs, and L&D partners to assess skill gaps, learning needs, validate instructional accuracy and capability development priorities.
- Conduct task analysis, workflow mapping, and learner assessments to determine instructional strategy.
- Execute end-to-end planning, design, development, and maintenance of learning solutions, including eLearning, instructor-led, virtual, and supporting resources.
- Design and develop high-quality learning content tailored to underwriting functions (e.g., Commercial risk assessment and Underwriting guidelines and authority structures)
- Recommend and build appropriate learning assets including eLearning, case studies, playbooks, as well as innovative learning approaches (e.g., simulations, adaptive learning, knowledge checks)
- Ensure all learning content reflects current underwriting practices, governance, and strategic priorities as well as aligns with enterprise-wide L&D instructional strategies and competency frameworks.
- Manage stakeholder expectations, timelines, and review cycles to ensure smooth development and deployment.
- Develop digital training using authoring tools such as Articulate Rise/Storyline, Captivate, Camtasia, or similar.
- Optimize courses for accessibility, mobile delivery, and user-friendly navigation.
- Leverage learning management systems (LMS) to deploy, track, and evaluate training.
- Apply evaluation models (Kirkpatrick or similar) to measure training impact on underwriting performance.
- Analyze learner feedback, assessment outcomes, and performance metrics to refine content.
- Maintain learning materials and knowledge repositories to ensure ongoing accuracy and relevance.
- Other duties as assigned.
Qualifications
- Degree or diploma in Instructional Design, Education, Adult Learning, or related field.
- 3–5+ years of experience designing corporate learning programs (experience in financial services or insurance preferred).
- Strong understanding of instructional design methodologies (ADDIE, SAM, etc.).
- Experience translating complex technical content into digestible learning experiences.
- Proficiency with eLearning authoring tools and multimedia editing software.
- Strong project management, communication, and collaboration skills.
- Familiarity with underwriting concepts is an asset (commercial insurance, risk assessment, pricing models, governance frameworks).
#LI-JB3 #LI-Hybrid
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.