Manager, Underwriting Operations, Commercial Mid-Market - Ontario

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Manager, Underwriting Operations, Commercial Mid-Market - Ontario

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

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: $130,000 - $150,000 . 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 Manager, Underwriting Operations, Commercial Mid-Market - Ontario is responsible for leading and developing a team of Commercial Mid-Market Underwriters while driving profitable growth, underwriting quality, and strong broker relationships across Ontario. This highly visible, market-facing leadership role combines people leadership, technical underwriting expertise, and business development support to strengthen Wawanesa's presence in the Ontario market.

Working closely with Business Development, Claims, Risk Prevention Services, Product, and Pricing, the Manager coaches underwriting talent, supports complex risk decisions, builds strategic broker partnerships, and ensures consistent execution of underwriting and growth strategies.

Key Responsibilities

• Lead, coach, and develop a high-performing underwriting team through regular coaching, file reviews, performance management, and talent development initiatives.
• Provide technical oversight on complex commercial risks, underwriting referrals, exceptions, and authority decisions while ensuring alignment with underwriting appetite and profitability objectives.
• Build and maintain strong broker relationships, participate in broker-facing meetings and growth initiatives, and represent Wawanesa as a trusted market leader throughout Ontario.
• Support profitable growth by partnering with Business Development on new business opportunities, targeted industries, and key broker relationships.
• Monitor portfolio performance, underwriting quality, and service standards, identifying trends and implementing corrective actions where required.
• Partner with internal stakeholders to execute commercial strategies, support underwriting and pricing initiatives, and contribute market insights to business decisions.
• Champion operational excellence, continuous improvement, regulatory compliance, and an exceptional broker experience.

Qualifications

• 8-10+ years of Commercial Underwriting experience, including significant Mid-Market expertise.
• Demonstrated leadership capability with a strong passion for coaching, mentoring, and developing underwriting talent.
• Strong technical knowledge of Commercial Property and Casualty risks, portfolio management, and underwriting authorities.
• Proven ability to balance profitable growth with disciplined underwriting practices.
• Strong broker relationship management, business development, and stakeholder engagement skills.
• Excellent communication, negotiation, and leadership abilities.
• CIP designation required; FCIP, CRM, or MBA considered assets.
• Willingness to travel throughout Ontario and occasionally nationally.

What Success Looks Like

Within the first 12 months, the successful candidate will have built a highly engaged underwriting team, strengthened broker relationships across Ontario, elevated underwriting quality and consistency, delivered profitable portfolio growth, and established themselves as a trusted technical and market leader within Commercial Mid-Market.

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.

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.

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