Bilingual Segment Specialist, Commercial Mid-Market (Farm)

Wawanesa Insurance•Montreal, QC

8d•CA$120,000 - CA$145,000•Hybrid

About The Position

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 [insert segment} 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 Director, Underwriting Operations, Commercial 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.

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

Nice To Haves

Product development and portfolio management experience considered an asset.
Bilingualism in English and French is considered an asset.

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, this will include 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
Working closely with Risk Preventions Services and Claims teams to drive compelling member propositions, solution 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.