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Underwriting Trainee, Small Business / Middle Market

Remote, USA Full-time Posted 2026-06-17

CNA Insurance is dedicated to developing its employees and offers a comprehensive Underwriting Trainee Program for individuals interested in a career in underwriting. Trainees will receive hands-on experience and training in underwriting practices, sales, and marketing skills while working closely with senior leadership.

Responsibilities

  • Learn underwriting practices by participating in formal and on-the-job training over their first 12 months with the organization
  • Have exposure to a diverse variety of accounts in different geographies, sizes, and complexity as they develop alongside others in their Trainee cohort
  • Interact with senior leadership
  • Evaluate a business by reviewing industry, business and government data, then deciding whether to accept or decline the risk
  • Responsible for pricing, as well as maintaining a steady flow of new and renewal business

Skills

  • Commitment to develop knowledge and understanding of underwriting
  • Strong sales aptitude
  • Effective analytical and problem-solving skills, good verbal and written communication skills, and the ability to learn rapidly
  • Excellent interpersonal skills, including an ability to influence, overcome obstacles and develop positive business relationships
  • Must be legally authorized to work in the United States without sponsorship now or in the future
  • Bachelor's degree with a minimum 3.0 GPA strongly preferred; equivalent experience considered

Benefits

  • Comprehensive and competitive benefits package
  • Help our employees – and their family members – achieve their physical, financial, emotional and social wellbeing goals

Company Overview

  • CNA is one of the largest U.S. commercial property and casualty insurance companies. It was founded in 1897, and is headquartered in Chicago, Illinois, USA, with a workforce of 5001-10000 employees. Its website is http://www.cna.com.
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