Director, Underwriting Operations, Commercial Small Business
Date: Dec 4, 2025
Location: North York - Toronto, ON (Hybr, CA Moncton, NB (Hybrid), CA Montreal, QC (Hybrid), CA Vancouver, BC (Hybrid), CA Winnipeg, MB (Hybrid), CA Ottawa, ON (Hybrid), CA Kitchener, ON (Hybrid), CA Edmonton, AB (Hybrid), CA Calgary, AB (Hybrid), CA Dartmouth, NS (Hybrid), CA
Company: Wawanesa Insurance
Job ID: 9606
Employment Type: New 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: $180,000 - $210,000. 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: Winnipeg, MB; Vancouver, BC; Calgary, AB; Edmonton, AB; Toronto (North York), ON; Kitchener, ON; Ottawa, ON; Montreal, QC; Quebec City, QC, Moncton, NB; Dartmouth; NS.
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
The Director, Underwriting Operations, Commercial Small Business has the dual responsibilities of overseeing an underwriting operations team in a newly nationalized structure while also bringing to life the future state of Commercial Small Business, prioritizing volume, speed and ease of doing business underpinned by levelling up capabilities in technology, portfolio management, artificial intelligence and pricing sophistication.
The incumbent will lead an Underwriting Operations group consisting of underwriters, technical specialists and supervisors across multiple regions and be accountable for growing income in Commercial Small Business through the speed and quality of underwriting decision-making.
Together with the VP, Commercial Small Business, the Small Business leadership team and other key stakeholders, the incumbent will co-architect the evolution of the Commercial Small Business underwriting process and then work with functional partners on driving to the future state while mobilising, engaging and coaching the Underwriting Operations team along this journey with passionate and authentic leadership.
Responsibilities
Operational Management
- Oversee underwriting processes, workflows, and governance to ensure accuracy, speed and ease of doing business.
- Standardize practices, procedures, and tools across regional underwriting teams to drive national alignment while maintaining regional expertise and broker service models.
- Monitor underwriting performance metrics and operational KPIs, implementing corrective action where needed.
- Lead continuous improvement initiatives focused on automation, digitization, and enhanced broker service.
Transformational Leadership
- Collaborate and provide input into the design and implementation of the transformation roadmap for Commercial Small Business.
- Move at pace by applying a test-and-learn approach, failing fast and pivoting quickly in response to learnings.
- Use effective collaboration and communication with key stakeholders to navigate roadblocks and governance processes.
People & Culture
- Empower, mentor, and develop a high-performing underwriting operations team in Commercial Small Business, fostering a culture of accountability, collaboration, and innovation.
- Attract and retain top talent, focussing on capabilities that will accelerate the transformation and thrive in the future state.
- Champion diversity, equity, and inclusion within the team and across the organization.
Collaboration & Influence
- Serve as a key liaison between underwriting, distribution, actuarial, claims, finance, and compliance functions.
- Build strong relationships with brokers and partners to ensure service expectations are met and exceeded.
Qualifications
- Minimum 10 years of experience in commercial insurance, with deep expertise in Small Business underwriting in the specific segment
- At least 5 years in a leadership role, preferably within a national insurer, with experience in cross-functional leadership and strategic execution
- Bachelor’s degree in business, insurance, risk management, or related field; MBA or CRM designations are considered strong assets.
- CIP or FCIP
- Experience with business transformation, data science, AI or digital technology considered an asset.
- Strong understanding of the small business markets, commercial lines regulatory frameworks, and distribution channels.
- Proven ability to grow income, with a focus on long-term portfolio health, proactively managing risk and building member value.
- Excellent relationship management, communication, and stakeholder engagement skills.
- Bilingualism in English and French is considered an asset.
- Ability and willingness to travel nationally to engage with regional teams and brokers.
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.
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Please note that 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.