Segment Specialist, Commercial Mid-Market; Manufacturing and Wholesale

Segment Specialist, Commercial Mid-Market (Manufacturing and Wholesale)

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.

Salary: The salary offered for this role is estimated to be within the following range: $120,000 - $145,000. It is part of a comprehensive offering that includes an annual bonus plan, leave of absence top‑up programmes, generous vacation time, personal days, premium free benefits and a pension plan.

The Segment Specialist, Commercial Mid-Market is responsible for working closely with the Director of Underwriting Operations to drive Wawanesa’s strategy, performance, and execution for the national Manufacturing & Wholesale portfolio. This role develops underwriting playbooks, analyzes performance, identifies growth and product development opportunities, and provides national technical leadership in underwriting, product development, pricing, risk selection and quality assurance.

• 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.
• Provide 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, solutions 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, and identify 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.

• 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 is considered an asset.
• Strong 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

We welcome applications from all qualified candidates, including racialised persons, women, Indigenous Peoples, persons with disabilities, members of the 2

SLGBTQIA+ community, gender‑diverse and neurodiverse individuals, and anyone who can contribute to the further diversification of thought and ideas.