Senior Field Underwriter, Commercial Mid-Market, Ontario

Wawanesa Insurance•North York, ON

7d•CA$120,000 - CA$140,000•Onsite

About The Position

The Senior Field Underwriter, Commercial Mid-Market is accountable for the profitable growth of a defined new business portfolio within an assigned territory. This role owns broker relationships, drives a disciplined new business pipeline development and conversion, exercises underwriting authority to secure new business aligned to risk appetite and portfolio strategy. This role operates with a high degree of autonomy within defined underwriting authority, making independent decisions on pricing, structure, and deal strategy for mid-market risks. This sale driven role balances new business production and relationship management with sound underwriting judgment, contributing to both immediate growth outcomes and the long-term sustainability and profitability of the mid-market portfolio.

Requirements

7-10+ years of commercial underwriting experience with strong mid-market exposure.
Successful track record of delivering profitable growth and managing broker relationships in a competitive broker distribution environment.
Proven ability to underwrite complex, multi-line accounts.
Strong technical expertise in relevant product line (property and casualty/farm/fleet) coverages, pricing, and wording interpretation.
Post-secondary education in Business, Finance, or related field; completed or actively pursuing a professional designation (CIP, FCIP, CRM, or equivalent).
Strong analytical, negotiation, and decision-making skills, proven ability to use sound judgement to evaluate risk and profitability.
Proficiency with Microsoft Office and ability to learn internal systems quickly.
Excellent relationship management, communication, presentation and stakeholder engagement skills in order to influence broker partners effectively.
Strong organizational skills with the ability to prioritize, multi-task, and meet deadlines.
Frequent travel is expected to support in person broker relationship management and visits; a fleet vehicle is provided, and a valid driver’s license with the ability to travel regularly within the assigned territory is required.

Nice To Haves

Bilingualism in English and French is considered an asset.

Responsibilities

Own and deliver new business growth targets through territory strategy, pipeline management, and broker engagement.
Drive pipeline conversion by proactively structuring deals and managing opportunities with key brokers.
Develop and execute territory strategies to increase broker penetration, win rates, and portfolio growth.
Exercise underwriting authority to assess, price, and structure complex mid-market risks.
Ensure alignment with underwriting guidelines, risk appetite, and portfolio quality while balancing growth objectives.
Document underwriting decisions, rationale, and risk mitigation strategies.
Apply market insights and pricing dynamics to develop competitive solutions and business cases.
Build and maintain strong broker relationships, acting as a trusted advisor and providing clear underwriting direction.
Identify growth opportunities within the broker portfolio aligned to segment strategy.
Represent the organization in broker meetings, industry events, and market engagements.
Gather and share competitor and market intelligence to inform strategy and improve positioning.
Collaborate with cross-functional partners and capture insights from lost or declined business to support continuous improvement and profitable growth.