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Commercial Transportation Underwriter

Canada, Hamilton 75000.00 - 105000.00 CAD / Year · Job Posted June 29, 2026
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Job Description

Our client is a growing and well-established Managing General Agent (MGA) specializing in commercial insurance solutions across Canada. Due to continued growth within their transportation portfolio, they are seeking a Commercial Lines Underwriter to join their underwriting team. This opportunity is ideal for an underwriting professional who enjoys working with complex commercial transportation risks, building strong broker relationships, and contributing to a collaborative, growth-oriented environment. The successful candidate will receive direct mentorship from experienced industry leaders while gaining exposure to specialized transportation and captive insurance programs.

Job Responsibility

  • Underwrite and manage a portfolio of medium to large commercial transportation and fleet accounts
  • Evaluate and quote new business, renewals, endorsements, and policy changes
  • Analyze risk exposures and make underwriting decisions within delegated authority levels
  • Negotiate terms, conditions, and pricing with broker partners
  • Build and maintain strong relationships with brokers and key stakeholders
  • Support profitable portfolio growth through sound underwriting practices
  • Provide technical guidance and mentorship to junior underwriting staff
  • Assist with the ongoing development and enhancement of underwriting guidelines, processes, and workflows
  • Collaborate with claims, operations, and leadership teams to ensure exceptional service delivery
  • Represent the organization at broker meetings, industry events, and networking functions as required

Requirements

  • Minimum 3 years of Commercial Auto or Commercial Transportation Underwriting experience
  • Experience underwriting medium to large transportation fleets preferred
  • Strong analytical and decision-making abilities
  • Excellent communication and relationship-building skills
  • Ability to thrive in a collaborative, fast-paced underwriting environment
  • CIP designation completed or in progress is preferred
  • RIBO license or willingness to obtain one is considered an asset
  • Exposure to domestic markets and Lloyd's placements is considered an asset

Nice to have

  • Experience underwriting medium to large transportation fleets preferred
  • CIP designation completed or in progress is preferred
  • RIBO license or willingness to obtain one is considered an asset
  • Exposure to domestic markets and Lloyd's placements is considered an asset

What we offer

  • $75,000 – $105,000 base salary + performance-based bonus
  • Comprehensive health and wellness benefits package
  • Retirement savings program
  • Generous paid time off
  • Tuition reimbursement and support for professional designations
  • Ongoing mentorship from experienced underwriting leaders
  • Collaborative team culture with strong internal support
  • Long-term career growth opportunities within a growing MGA platform

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