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// POSTED: Apr 14, 2026

Middle & Large Business Underwriting Associate / Trainee - Boston, MA or Hartford, CT

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The Hartford is an insurance company dedicated to helping people protect what matters most to them. They are seeking an Underwriting Associate/Trainee to join their team, where the role focuses on providing the right coverage for customers and developing underwriting skills through a comprehensive training program. Responsibilities - Gain Real World Experience - Collaborate with sales teams, experienced underwriters, and other leaders - Participate in the Commercial Underwriter Onboarding and Risk Education (CORE) development program - Engage in self-directed and virtual classroom learning sessions - Obtain on-the-job work experience and integrated sales training - Demonstrate a customer-first mindset - Analyze data and employ critical thinking skills - Build relationships and trust among diverse groups - Make decisions and follow through on commitments - Navigate a fluid and changing business environment Skills - Bachelor's Degree preferred, or equivalent combination of education, training, and Insurance experience - Up to 3 years of Insurance experience preferred - Excellent written and interpersonal communication and presentation skills - Ability to think analytically about business problems, make recommendations, and propose solutions - Possession of resilience and an entrepreneurial spirit - Demonstration of solid time, organizational, and desk management skills - Goal oriented with a strong desire to deliver outcomes in timely manner - Acts with a sense of urgency and is responsive to internal and external customer needs - Strong sales skills with the ability to negotiate and sell all messages including with those that may be difficult - Challenge the status quo to implement improvement and compete to win - A valid driver's license is required, as use of a company pool car will be necessary for periodic travel - Demonstrates satisfactory progress during the Training Program and achieve passing scores on all tests, case studies, and foundational underwriting assessments - Potential to travel during training may exist Benefits - Short-term or annual bonuses - Long-term incentives - On-the-spot recognition Company Overview - The Hartford is an industry leading provider of property and casualty insurance, group benefits and mutual funds. It was founded in 1810, and is headquartered in Hartford, Connecticut, USA, with a workforce of 10001+ employees. Its website is http://www.thehartford.com.
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