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About the Role

The Senior Underwriting Training Specialist - Commercial Insurance plays a key role in creating, updating, and implementing an underwriting training program for the Commercial Insurance sector. The successful candidate will support the effectiveness and execution of the underwriting strategy and act as a critical bridge between underwriting, operations, and business stakeholders.

Responsibilities

• Lead the design, development, and implementation of underwriting learning experiences for the Commercial Insurance sector by determining how to best scale programs and ensuring appropriate training methods are selected to best support Commercial Insurance teams.
• Create clear and consistent underwriting communications, tailored to the audience, related to these learning experiences, ensuring complex concepts are translated into practical, easy-to-use tools.
• Develop and maintain underwriting training roadmaps by conducting needs analysis and using it to ensure training meets the needs of internal stakeholders.
• As a subject matter expert, lead the development, creation, and distribution of other training and communication materials to support the effectiveness of underwriting operations.
• Oversee the design, implementation, and ongoing management, including governance structure, of an Underwriting Knowledge Site containing processes, training, and other resources for the department and other stakeholders.
• Regularly review existing training programs, integrations, underwriting knowledge, and resources to ensure they are relevant, clear, concise, and up-to-date.
• Support underwriting transformation initiatives (e.g., appetite changes, process changes).
• Coach and develop team members by sharing knowledge and best practices that foster a culture of continuous learning and improvement.
• Monitor both industry trends and underwriting performance, including legislative and regulatory changes.
• Ensure participation, engagement, success, and qualitative feedback on learning and communication initiatives.
• Determine metrics and provide timely, meaningful, and accurate reporting on learning effectiveness, including participation and completion.
• Build and maintain productive business relationships by liaising with internal and external stakeholders.
• Act as a subject matter expert on Commercial Insurance underwriting initiatives to enhance underwriting expertise and critical thinking.

Requirements

• At least five years of experience in the Property & Casualty insurance industry with a significant focus on training, enablement, or knowledge transfer OR experience in learning and development within the insurance or financial services industry.
• Knowledge or experience in Commercial Insurance underwriting and related best practices, either in a learning and development context or a functional area.
• Proven ability to design, develop, adapt, and maintain training programs by leveraging knowledge of adult learning practices.
• Post-secondary education and/or CIP designation or equivalent designation in the Property & Casualty insurance industry.
• Critical thinking and logical, critical reasoning and sound judgment.
• Excellent analytical and problem-solving skills; ability to analyze information in detail and select and implement the best solutions in a timely manner.
• Excellent communication and presentation skills, with the ability to present a variety of complex content at an appropriate level for the target audience.
• Strong planning and organizational skills; ability to develop effective plans that consider priorities and outline activities, resources, and timelines.
• Agile and change-ready to support transformation initiatives, innovation, and strategic direction.
• Comfortable working on digital platforms, both for content publishing and management.

Skills

• Adult learning practices
• Underwriting
• Commercial Insurance
• Training design
• Training development
• Training implementation
• Needs analysis
• Communication
• Presentation
• Planning
• Organization
• Analytical skills
• Problem-solving
• Critical thinking
• Digital platforms

Location

• Winnipeg, MB
• Wawanesa, MB
• Vancouver, BC
• Calgary, AB
• Edmonton, AB
• Lethbridge, AB
• Toronto (North York), ON
• Kitchener, ON
• Ottawa, ON
• Montréal, QC
• Ville de Québec, QC
• Moncton, NB
• Dartmouth, NS

Work Type

• Hybrid
• Remote
• Onsite

Experience Level

• Senior
• Five years of experience

Education Level

• Post-secondary education
• CIP designation or equivalent
• Adult Education Certificate (CAE, CACE) - asset

Salary/Compensations

• $95,000 - $120,000

Benefits

• Annual incentive program
• Supplemental leave program
• Generous vacation days
• Personal days
• Premium-free benefits
• Pension plan

About the Company

• Wawanesa offers a hybrid work environment providing flexibility for employees to balance working in the office (2 days per week OR 15 hours per week in a Wawanesa office) and working remotely.
• The Wawanesa Mutual Insurance Company ('Wawanesa'), founded in 1896, is one of Canada's largest insurers, generating over $3.5 billion in annual revenue and holding $10 billion in Canadian assets.
• Headquartered in Winnipeg, The Wawanesa Mutual Insurance Company is the parent company of Wawanesa Life, which provides life insurance products and services across Canada, and Western Financial Group, which insures individuals and businesses across the country.
• Wawanesa is proud to serve over 1.7 million members in Canada and has over 3,300 employees across the regions and communities where it operates.
• We support organizations that strengthen communities, donating over $3.5 million annually to charities, including over $2 million annually to support those on the front lines of climate change.
• We are also proud to be recognized as one of Manitoba's Top Employers.
• We are currently seeking a dedicated, driven, enthusiastic individual who is eager to thrive in a constantly changing environment, seeking an opportunity to gain diverse experiences and grow within a rapidly expanding team.

Equal Opportunity

• Wawanesa is committed to Diversity, Equity, Inclusion, and Belonging (DEIB) and believes our strength lies in our diverse workforce, resulting in a workforce representative of the population as a whole.
• We encourage all qualified applicants to apply, whether they are racialized people, women, Indigenous people, persons with disabilities, members of the 2ELGBTQIA+ community, persons of diverse gender identities, and neurodiverse persons, or anyone who may contribute to further diversification of perspectives and ideas.
• We want to ensure our recruitment process is accessible to all candidates. If you require accommodation during the recruitment process, please feel confident emailing jobs@wawanesa.com.
• All applicants for employment with Wawanesa are subject to the applicable Employee Personal Information Policy.
• Please note that as part of this recruitment process, AI tools may be used to screen, assess, or select applications. All final decisions are made after review by recruiters and hiring managers, in accordance with all applicable laws.