Date: Jul 24, 2026
Location: North York - Toronto, ON (Hybr, CA
Company: Wawanesa Insurance
Job ID: 10142
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: $120,000 - $140,000 . 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
The Senior Field Underwriter, Commercial Mid-Market is accountable for the profitable growth of a defined new business portfolio within an assigned territory. This role owns broker relationships, drives a disciplined new business pipeline development and conversion, exercises underwriting authority to secure new business aligned to risk appetite and portfolio strategy. This role operates with a high degree of autonomy within defined underwriting authority, making independent decisions on pricing, structure, and deal strategy for mid-market risks. This sale driven role balances new business production and relationship management with sound underwriting judgment, contributing to both immediate growth outcomes and the long-term sustainability and profitability of the mid-market portfolio.
Job Responsibilities
Own and deliver new business growth targets through territory strategy, pipeline management, and broker engagement.
Drive pipeline conversion by proactively structuring deals and managing opportunities with key brokers.
Develop and execute territory strategies to increase broker penetration, win rates, and portfolio growth.
Exercise underwriting authority to assess, price, and structure complex mid-market risks.
Ensure alignment with underwriting guidelines, risk appetite, and portfolio quality while balancing growth objectives.
Document underwriting decisions, rationale, and risk mitigation strategies.
Apply market insights and pricing dynamics to develop competitive solutions and business cases.
Build and maintain strong broker relationships, acting as a trusted advisor and providing clear underwriting direction.
Identify growth opportunities within the broker portfolio aligned to segment strategy.
Represent the organization in broker meetings, industry events, and market engagements.
Gather and share competitor and market intelligence to inform strategy and improve positioning.
Collaborate with cross-functional partners and capture insights from lost or declined business to support continuous improvement and profitable growth.
Qualifications
7-10+ years of commercial underwriting experience with strong mid-market exposure.
Successful track record of delivering profitable growth and managing broker relationships in a competitive broker distribution environment.
Proven ability to underwrite complex, multi-line accounts.
Strong technical expertise in relevant product line (property and casualty/farm/fleet) coverages, pricing, and wording interpretation.
Post-secondary education in Business, Finance, or related field; completed or actively pursuing a professional designation (CIP, FCIP, CRM, or equivalent).
Strong analytical, negotiation, and decision-making skills, proven ability to use sound judgement to evaluate risk and profitability.
Bilingualism in English and French is considered an asset.
Proficiency with Microsoft Office and ability to learn internal systems quickly.
Excellent relationship management, communication, presentation and stakeholder engagement skills in order to influence broker partners effectively.
Strong organizational skills with the ability to prioritize, multi-task, and meet deadlines.
Frequent travel is expected to support in person broker relationship management and visits; a fleet vehicle is provided, and a valid driver’s license with the ability to travel regularly within the assigned territory is required.
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.
