Underwriter Trainee Jobs in Springfield, MA (NOW HIRING)

We're determined to make a difference and are proud to be an insurance company that goes well beyond coverages and policies. Working here means having every opportunity to achieve your goals - and to help others accomplish theirs, too. Join our team as we help shape the future.

Underwriting Trainee Opportunities: Gain Real World Experience

As a participant in the Small Business Underwriter On-boarding and Risk Education training program, you will gain critical experience to prepare you for a successful underwriting career at The Hartford.

Your underwriting career here means collaboration, inclusivity, innovative thinking and so much more. Here, we value entrepreneurial spirits, self-starters and are customer focused. We welcome all ideas and encourage authenticity. It's where opportunities exist to hone your underwriting skills by working with our sales teams, experienced underwriters, and other leaders - and your career path can take any direction you might choose.

Our 14-week hybrid training program starting October 2026 includes self-directed and virtual classroom learning sessions. You will receive on-the-job work experience as well as ongoing coaching and support from your mentor and manager to round out your Small Business Underwriting experience. After the formal program concludes, you will have the knowledge to begin a formal career with full support every step of the way.

AS AN ASSOCIATE UNDERWRITER YOU WILL:
Work on our underwriting team supporting small business owners. The underwriter will handle all commercial lines, including Business Owner's Policy (BOP), Commercial Automobile, Workers' Compensation and Umbrella.
Learn to accurately develop and price individual risks, analyze loss and risk information, and recognize "red flags" and file inconsistencies to write profitable commercial business.
Partner with aligned territory sales rep to achieve profit and growth objectives.
Learn to build and leverage relationships with key agents that allow The Hartford to obtain new accounts and drive optimal business results in a highly competitive marketplace.

You Will Be a Good Match if You Have:
A customer-first mindset, putting our customers at the center of everything you do.
A passion for making decisions by 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.
The ability to advance your career into technical OR leadership positions.

Qualifications:
Bachelor's Degree; prior 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.
Demonstrates satisfactory progress during the Training Program and achieve passing scores on all tests, case studies, and foundational underwriting assessments.
Flexibility to travel approximately 10% of the time.

The Small Business Underwriting team supports customers and agents countrywide so candidates must be available to work the below schedules:
Charlotte, NC: 8:00AM - 5:00PM EST.
Clinton, NY: 8:00AM - 5:00 PM EST.
Hartford, CT: 8:00AM - 5:00 PM EST.
San Antonio, TX: 10:00AM - 7:00 PM CST.
Scottsdale, AZ: 9:00AM - 6:00PM MST.

- Location: hybrid reporting to Charlotte, NC; Clinton, NY; Hartford CT; San Antonio, TX or Scottsdale, AZ

Sustaining The Hartford's unique workplace culture is vital to delivering on our purpose - underwriting human achievement - and continuously producing outstanding results. Our enterprise work model, which reflects a mix of in-office, hybrid and fully remote roles, helps us attract, retain and develop the talent we need to achieve the company's strategic goals. This role will have a Hybrid work arrangement.

Compensation

The listed annualized base pay range is primarily based on analysis of similar positions in the external market. Actual base pay could vary and may be above or below the listed range based on factors including but not limited to performance, proficiency and demonstration of competencies required for the role. The base pay is just one component of The Hartford's total compensation package for employees. Other rewards may include short-term or annual bonuses, long-term incentives, and on-the-spot recognition. The annualized base pay range for this role is:

Equal Opportunity Employer/Sex/Race/Color/Veterans/Disability/Sexual Orientation/Gender Identity or Expression/Religion/Age

About Us|Our Culture|What It's Like to Work Here|Perks & Benefits