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About the Role

The Segment Specialist, Commercial Mid-Market drives Wawanesa’s strategy, performance, and execution for the national commercial mid-market portfolio. This role focuses on developing underwriting playbooks, analyzing performance, identifying growth and product development opportunities, and providing national technical leadership in underwriting, product development, pricing, risk selection, and quality assurance to ensure portfolio quality, profitability, and competitiveness.

Responsibilities

Support the development of underwriting playbooks for the defined mid-market segment, ensuring the portfolio is positioned for profitable growth, operational excellence, and superior service.
Support the development of underwriting standards, tools, pricing strategies, and risk management practices tailored to the complexity and scale of the specific segment.
Act as a technical expert for the specific segment, supporting the underwriting of large accounts, performing file reviews, large loss analysis, portfolio reviews and coaching underwriters while holding high underwriting authority for the business segment.
Collaborate with actuarial, analytics, and data teams to ensure pricing reflects risk exposure, competitive benchmarks, and emerging trends in the mid-market segment.
Partner with product development teams to evolve mid-market offerings, introducing solutions that respond to broker and member needs and drive profitable growth.
Work closely with Risk Preventions Services and Claims teams to drive compelling member propositions, solutions, and efficiencies enabling brokers to sell Wawanesa as a market of choice.
Support the director in providing technical leadership to middle market underwriters fostering a high-performance and purpose-driven culture that drives profitable growth while driving underwriting quality and pricing adequacy.
Ensure the portfolio is underpinned by sound governance, underwriting discipline, and compliance with all applicable regulatory and corporate policies.
Align operations and underwriting guidelines with claims strategies to drive consistent outcomes and ensure fair, member-centric experiences.
Support the director in monitoring and reporting on key portfolio performance metrics for the specific segment—hit ratio, loss ratio, growth, retention, mix, and broker performance—while identifying opportunities for growth, diversification and loss ratio improvement.
Embed Wawanesa’s purpose and values into all aspects of leadership—building trust with members, enabling success for brokers, and creating value for communities.
Promote inclusion, integrity, and fairness in how business is conducted, decisions are made, and teams are developed.

Requirements

Minimum 10 years of experience in commercial insurance, with deep expertise in mid-market underwriting in the specific segment.
Good communication skills in French and English, both written and spoken.
Holds CIP or FCIP.
Strong understanding of the mid-market business environment, commercial lines regulatory frameworks, and broker distribution models.
Proven ability to balance growth and risk, with a focus on long-term portfolio health and member value.
Excellent relationship management, communication, and stakeholder engagement skills.
Ability and willingness to travel nationally to engage with regional teams and brokers.

Skills

Product development
Portfolio management
Bilingualism in English and French

Location

Toronto (North York), ON
Kitchener, ON
Ottawa, ON
Montreal, QC
Quebec City, QC
Moncton, NB
Dartmouth, NS

Work Type

Hybrid
Remote
Onsite

Experience Level

Minimum 10 years of experience

Education Level

Bachelor’s degree in business, insurance, risk management, or related field
MBA or CRM designations are considered strong assets

Salary/Compensations

$120,000 - $145,000

Benefits

Annual bonus plan
Leave of absence top-up programs
Generous vacation time
Personal days
Premium free benefits
Pension plan

About the 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 is 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.

Equal Opportunity

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.
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.