Wawanesa InsuranceVerified Job Source

Senior Underwriting Training Specialist - Commercial Lines

Calgary, AB
Hybrid
Posted Sep 27, 2026
1 position

$95,000–$120,000 / year

Opens an external site

Employment type: Full-time
Experience level: Senior · 5+ years
Minimum education: Professional degree
Posting language: English
Working hours: 15 hours per week
Office presence: 2 days per week

Job summary

The Senior Underwriting Training Specialist leads the design, development, and implementation of underwriting learning experiences for Commercial Lines. This role acts as a subject matter expert to bridge the gap between underwriting strategy, operations, and enterprise stakeholders.

Job details

Job ID: 10015 Employment Type: New RoleWorking 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 UsAt 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 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 and utilizing needs analysis to ensure training meets the needs of internal stakeholders. Lead as a subject matter expert, the development, creation, and distribution of other training and communication materials to assist with efficiency and effectiveness in underwriting activities. Oversee the design, implementation, and continuous management, including governance structure of an underwriting knowledge site containing processes, training, and other resource materials to be used by department and other stakeholders. Maintain through regular review of existing training programs, onboarding, underwriting knowledge, and resource to ensure it is relevant, clear, concise, and current. Support underwriting transformation initiatives (e.g., appetite shifts, process changes) Mentor and develop team members through the sharing of knowledge and best practices that fosters a culture of continuous learning and improvement Monitor both internal industry trends and underwriting performance, including legislation and regulation changes, and track participation, engagement, success and qualitative feedback on learning and communication initiatives. Identify metrics and provide timely, meaningful, and accurate reporting on learning effectiveness including participation and completion statistics. Develop and enhance productive business relationships by liaising with internal and external stakeholders. Lead as a subject matter expert (SME) in Commercial lines underwriting initiatives focused on enhancing underwriting expertise and critical thinking. Qualifications 5+ years Property and Casualty industry experience with a strong focus on training, enablement or knowledge sharing. Knowledge and/or background in Commercial underwriting and related best practices, within a learning and development context and/or functional area. Proven ability to design, develop, scale, and sustain training programs leveraging knowledge of adult learning practices. Post-secondary education and/or completed CIP or equivalent Property and Casualty industry designation. Certificate in Adult Education (CAE, CACE) is considered an asset. Ability to use critical thinking, logic, critical reasoning, and good judgement. Excellent analytical and problem-solving skills, with the ability to conduct detailed analysis of information and to select and implement best solutions in a timely manner. Excellent communication and presentation skills, with the ability to present varying degrees of complex information at a level appropriate for the audience. Strong planning and organizing skills, with the ability to develop and prioritize effective plans that define activities, resources, and timelines. Agile and change-ready to support transformation initiatives, support change and strategic direction. Comfortable working on digital platforms, both publishing and managing content. #LI-WAWA Diversity Equity, Inclusion & BelongingAt 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.

What you’ll do

Requirements

Candidates must have 5+ years of Property and Casualty industry experience with a focus on training or knowledge sharing. A post-secondary education and/or a CIP designation is required, with a certificate in Adult Education considered an asset.