Senior Underwriter - Commercial Lines, Mid-Market, Ontario

Wawanesa Insurance; Toronto; On-site; CAD 80,000 - 100,000; Full time

Benefits offered by this job

Annual bonus plan

Leave/top-up programs

Generous vacation time

Premium free benefits

Pension plan

Job summary

The Wawanesa Mutual Insurance Company in Toronto, ON is seeking a Senior Underwriter for Commercial Lines to analyze complex high‑premium business and collaborate with the sales force. You will provide expert guidance, ensure policy data integrity, and mentor junior staff while supporting continuous process improvements.

This head-office role requires strong English communication across Canada, with a hybrid work arrangement and a competitive compensation package including an annual bonus plan

Qualifications

• Five years Property and Casualty industry experience.
• Post-secondary education or related business experience.
• Completed or actively pursuing a Property and Casualty Industry Designation.
• Working knowledge of Microsoft Office Suite.
• Excellent attention to detail with the ability to review information carefully and comprehensively.
• Excellent communication skills with the ability to present information in a convincing manner.

Responsibilities

• Perform risk analysis using technology and external data sources for quoting, negotiating and authorizing acceptance of risk.
• Arrange reinsurance or subscribing companies where appropriate.
• Determine eligibility for policy renewals based on guidelines and retention goals.
• Maintain accurate records of decisions and completeness of policy data.
• Communicate decisions and respond to requests in a prompt and professional manner.
• Act as a subject matter expert for insurance policies, processes, regulations and audit.
• Mentor and train less experienced team members.
• Participate in periodic work reviews for quality assurance purposes.
• Support the development and implementation of business change.
• Ensure efficient handling of work assignments, including calls.
• Influence team members in a positive manner and provide short term direction towards goals.

Job description

Job ID: 10178

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: Toronto (North York), ON; Kitchener, ON; Ottawa, ON.

Working Business Language: English. This role is considered a head-office role and will be required to communicate with internal stakeholders across Canada where the primary business language utilized is 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 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

Working under minimal supervision, the Senior, Underwriter, 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

• Perform risk analysis using technology as well as external data sources for the purposes of quoting, negotiating and authorizing the acceptance of risk.
• Arrange reinsurance or subscribing companies where appropriate.
• Determine eligibility for policy renewals based on guidelines and retention goals of the company.
• Maintain accurate records of decisions made and maintain completeness of policy data.
• Communicate decisions, and respond to requests in a prompt and professional manner.
• Act as a subject matter expert for insurance policies, processes, regulations and audit.
• Mentor and train less experienced team members.
• Participate in periodic work reviews for quality assurance purposes.
• Support the development and implementation of business change.
• Ensure efficient handling of work assignments, including calls.
• Influence team members in a positive manner, and provide short term direction effectively working towards team goals.
• Foster positive working relationships with internal and external parties, including networking at industry events.
• Perform other duties as assigned.

Qualifications

• Five years Property and Casualty industry experience.
• Post-secondary education or related business experience.
• Completed or actively pursuing a Property and Casualty Industry Designation.
• Working knowledge of Microsoft Office Suite.
• Excellent attention to detail with the ability to review information carefully and comprehensively.
• Excellent decision making skills with the ability to provide justification.
• Excellent communication skills with the ability to present information in a convincing manner.
• Excellent customer service skills.
• Strong analytical and problem solving skills with the ability to identify and implement solutions.
• Adapts to change and performs effectively under pressure.
• Ability to multi-task and monitor progress to meet deadlines.

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 [e-mail]. 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.