Manager, Underwriting Operations - Commercial Small Business

Job ID: 10349 

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: Winnipeg, MB; Wawanesa, MB; Vancouver, BC; Calgary, AB; Edmonton, AB.

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: $100,000 - $130,000. 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, 100% owned by its members, with more than $4.1 billion in annual revenue and $12.5 billion in assets. Headquartered in Winnipeg, Wawanesa is the parent company of Wawanesa Life, which provides life insurance solutions throughout Canada, and Western Financial Group, a leading national distributor of personal and business insurance. In March of 2026, Wawanesa entered into an agreement to acquire Everest Insurance Company of Canada to strengthen its commercial insurance capabilities and advance its long-term growth strategy.

Wawanesa proudly serves more than 1.8 million members and we are home to more than 3,000 employees across Canada. The company actively gives back to organizations that strengthen communities, donating more than $4 million annually to charitable organizations, including more than $2 million each year in support of people on the front lines of climate change. Learn more at 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

In this role, the Manager of Underwriting Operations in Commercial Small Business (West) is responsible for working closely with the CL SME Directors, supporting the strategic direction, operational effectiveness, and performance of the Small Business underwriting portfolio. The role provides leadership, technical guidance, and business expertise to achieve targeted business results while fostering a culture of collaboration, continuous improvement, and exceptional customer service nationally. 

Job Responsibilities

• Monitor portfolio performance and underwriting workflow to support the achievement of short- and long-term business objectives.
• Evaluate economic, industry, and market conditions for potential or current impacts to business performance and collaborate with the CL SME Leadership team to recommend appropriate actions. 
• Lead and provide mentorship by finding opportunities in providing coaching, technical guidance, and development support to underwriting professionals to enhance performance, engagement, and capability.
• Promote adherence to underwriting guidelines, policies, procedures, and regulatory requirements.
  Influence underwriting practices and culture while supporting the organization's risk appetite and profitability objectives.
• Champion the development, implementation, and adoption of business initiatives, process improvements, and operational changes.
• Assess complex risks and provide recommendations to support sound underwriting decisions.
• Foster strong working relationships with internal and external stakeholders, including brokers, business partners, regional offices, and industry contacts.
• Represent the Small Business underwriting function on cross-functional projects, committees, and strategic initiatives.
• Perform other duties as assigned. 

Qualifications

• 5-7 years Commercial Property and Casualty, Auto or Farm industry experience.
• ​Post-secondary education and/or completion of a Property and Casualty Industry Designation
• ​Strong leadership skills with the ability to motivate and engage high performing teams while managing change.
• ​Excellent negotiation skills with the ability to present information or contradictory perspectives with sound influence.
• ​Excellent analytical and problem-solving skills with the ability to select and implement best solutions.
• ​Excellent decision-making skills with the ability to provide justification.
• ​Excellent communication skills with the ability to present information in a convincing manner.
• ​Excellent 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.