Job title: Transportation Insurance Senior Underwriting Assistant
Job type: Permanent
Emp type: Full-time
Industry: Insurance
Functional Expertise: Underwriting Assistant
Location: Chicago, IL
Job published: 12/09/2025
Job ID: 147181

Job Description

Transportation Senior Underwriting Assistant

Job Summary

Seeking a highly motivated and detail-oriented Transportation Senior Underwriting Assistant to join a dynamic team. This role is an excellent opportunity to contribute to a growing organization that is a leader in the wholesale insurance industry. The ideal candidate will have a strong background in underwriting support, particularly in the transportation vertical, and will play a key role in quoting new and renewal business while collaborating with assigned agents on policies.

Compensation Package

  • Salary Range: $60,000 - $70,000 annually
  • Bonus: Semi-annual performance-based bonus
  • Benefits: Comprehensive benefits package

Responsibilities

  • Provide underwriting support for the transportation vertical, handling both small and large fleet accounts.
  • Quote new and renewal business efficiently and accurately.
  • Collaborate with assigned agents to manage new and existing policies.
  • Ensure compliance with company policies and industry regulations.
  • Maintain accurate records and documentation for all underwriting activities.

Qualifications/Requirements

  • Minimum of 4+ years of experience in underwriting support, preferably within the transportation sector.
  • Property & Casualty (P&C) licensure/designation is required.
  • Strong understanding of transportation accounts, including small and large fleet policies.
  • Proficiency in quoting new and renewal business.
  • Excellent communication and organizational skills.
  • Ability to work independently and collaboratively in a fast-paced environment.
  • Flexibility to travel to the local office 1-2 times per month.

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