Job ID: 10121

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: Winnipeg, MB; Wawanesa, MB; Vancouver, BC; Calgary, AB; Edmonton, AB; Lethbridge, AB; Toronto (North York), ON; Kitchener, ON; Ottawa.

Working Business Language: English. Any required communication across Canada is in English. Full proficiency in English required.

Salary: At Wawanesa, salary is only one component of a holistic, comprehensive and competitive offering. 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 is estimated to be within the following range: $120,000 - $145,000. Candidates with salary expectations outside of the range are still encouraged to apply.

Job Overview

The Segment Specialist, Commercial Mid-Market is responsible for working closely with the Director, Underwriting Operations, Commercial Mid-Market to drive Wawanesa’s strategy, performance, and execution for the national Manufacturing & Wholesale portfolio. Targeting commercial policies ranging from $10K to $500K in premium, this role is responsible for developing underwriting playbooks, analyzing performance, identifying growth and product development opportunities for the defined mid-market business segment, and provides national technical leadership in underwriting, product development, pricing, risk selection, and quality assurance for the specified segment, ensuring portfolio quality, profitability and competitiveness for the defined segment/portfolio. Reporting to the VP, Commercial Lines, Mid-Market this creative, solution oriented, technical underwriter works close partnership with middle market underwriters to undertake competitive research, develop solutions, identify opportunities, and ensure portfolio quality, and profitability while maintaining a competitive edge.



This role will hold high underwriting authority for the business segment and provides technical leadership and coaching to underwriters to get complex deals over the line.

Job Responsibilities

- Support the development of underwriting strategies, standards, tools, and pricing approaches for the mid-market segment, ensuring alignment with risk exposure, competitive benchmarks, and emerging trends to drive profitable growth and operational excellence
- Act as a technical expert for the segment, supporting large account underwriting, file and portfolio reviews, and large loss analysis, while providing coaching and technical leadership to underwriters to strengthen underwriting quality and pricing adequacy
- 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 Prevention Services and Claims teams to drive compelling member propositions, solution and efficiencies enabling brokers to sell Wawanesa as a market of choice
- 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 VP 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

Qualifications

- Minimum 10 years of experience in commercial insurance, with deep expertise in mid-market underwriting in the specific segment
- Bachelor’s degree in Business, Insurance, Risk Management, or a related field, along with a CIP or FCIP designation; an MBA or CRM designation is considered a strong asset
- Product development and portfolio management experience considered an asset
- Robust understanding of the mid-market business environment, commercial lines regulatory frameworks, and broker distribution models
- Experience underwriting mid-market commercial risks, with exposure to Manufacturing and Wholesale segments strongly preferred
- 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
- 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

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.

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📌 Segment Specialist, Commercial Mid-Market (Manufacturing and Wholesale) (Winnipeg)
🏢 Wawanesa Insurance
📍 Winnipeg