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

Posted 2026-05-06
Remote, USA Full-time Immediate Start

The Hartford is an insurance company dedicated to helping people protect what matters. The role of Underwriting Associate involves gaining real-world experience through a comprehensive training program, collaborating with teams, and developing underwriting skills to provide customers with appropriate coverage.


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 as well as integrated sales training
  • Follow through on commitments and own your work
  • Build relationships and trust among diverse groups
  • Analyze data and employ critical thinking skills to make decisions
  • Challenge the status quo to implement improvement and compete to win

Skills

  • A customer-first mindset, putting our customers at the center of everything you do
  • A passion for making decisions through both analyzing data and employing critical thinking skills
  • A team spirit and desire to work collaboratively
  • A financial mindset to help make the best decisions
  • Ability to own your work and following through on commitments
  • Ability to decipher and execute within a fluid and changing business environment
  • An understanding of how to build relationships and trust among diverse groups
  • 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
  • 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
  • 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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