Date: Jun 8, 2026
Location: North York - Toronto, ON (Hybr, CA Kitchener, ON (Hybrid), CA
Company: Wawanesa Insurance
Job ID: 9920
Employment Type:
Existing 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: $80,000 - $100,000 . 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: Toronto (North York), ON; Kitchener, ON; Ottawa, ON, Dartmouth, NS; Moncton, NB.
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 Automobile Underwriting Midmarket Commercial Lines is responsible for analyzing the acceptability of complex and high premium volume business according to company guidelines by working collaboratively with our sales force and providing value added expertise and service to both potential and existing policyholders.
Job Responsibilities
Fleet & Garage Management and Analysis: You will be responsible for risk analysis using technology as well as external data sources for the purposes of quoting, negotiating and authorizing the acceptance of risk.
Knowledge Sharing: You will actively contribute to the team's ongoing training by sharing your knowledge and expertise to promote collective excellence.
Portfolio Development in Ontario & Maritimes: You will contribute to the strategic development of our portfolio in the Ontario & Maritimes region, working closely with our broker partners and internal stakeholders.
Rapidly Growing Region and Department: By joining a rapidly expanding department, you will benefit from personal and professional development opportunities while playing a key role in achieving business objectives.
Participation in Fleet Development: You will be involved in the evolution and management of the fleet for Wawanesa's Commercial Insurance department, directly contributing to our growth and success.
Networking and Collaboration: You will maintain excellent relationships with our broker partners, participating in industry events to exchange ideas and promote Wawanesa's expertise.
Pricing and Renewal Management: You will assess policy renewal eligibility according to the company's guidelines, while aiming to strengthen customer retention.
High-level customer service: Serve as a key point of contact, offering professional, expert, and proactive service.
Qualifications
Minimum of 5 years of Commercial Auto Underwriting Experience (Fleet & Garage)
Post-secondary education or related business experience.
Completed or actively pursuing a Property and Casualty Industry Designation (eg: CIP).
Working knowledge of Microsoft Office Suite and underwriting software.
Excellent attention to detail with the ability to review information carefully and comprehensively.
Strong analytical and problem-solving skills with the ability to provide justification.
Strong interpersonal skills and ability to present information in a convincing manner.
Ability to multi-task and prioritize daily work while meeting deadlines and maintaining a high level of performance.
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
[email protected] .
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.
