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Underwriting Trainee Jobs in Springfield, MA (NOW HIRING)

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Underwriting Trainee information

See Springfield, MA salary details

$32.4K

$78.6K

$139K

How much do underwriting trainee jobs pay per year?

As of Jul 4, 2026, the average yearly pay for underwriting trainee in Springfield, MA is $78,602.00, according to ZipRecruiter salary data. Most workers in this role earn between $60,800.00 and $86,700.00 per year, depending on experience, location, and employer.

What is the difference between Underwriting Trainee vs Underwriter?

AspectUnderwriting TraineeUnderwriter
CredentialsTypically entry-level, may require a degree in finance, insurance, or related fieldProfessional certification often preferred, such as CPCU or similar
Work EnvironmentTraining programs, supervised tasks, learning-focusedDecision-making, risk assessment, independent or team-based
Job ResponsibilitiesAssisting in risk evaluation, learning underwriting processesEvaluating risks, approving or rejecting policies

In summary, an Underwriting Trainee is an entry-level role focused on learning and supporting underwriting tasks, while an Underwriter is a fully responsible professional making risk decisions independently.

What are Underwriting Trainees?

Underwriting Trainees are entry-level professionals who are learning how to evaluate insurance applications, assess risks, and determine appropriate coverage and premiums. They work under the supervision of experienced underwriters and receive training in company policies, industry regulations, and risk assessment techniques. The goal of an underwriting trainee is to develop the skills necessary to make sound decisions regarding accepting or rejecting insurance applications and to eventually become a fully qualified underwriter.

What kind of training and mentorship can an Underwriting Trainee expect during their first year?

As an Underwriting Trainee, you can expect a structured onboarding process that combines classroom learning with hands-on experience. Most insurance companies pair trainees with experienced underwriters or mentors who provide guidance on risk assessment, policy review, and client interactions. You’ll likely rotate through different insurance lines to gain a broad understanding of underwriting practices, and participate in team meetings to discuss real cases. This collaborative environment helps you build technical skills and professional networks, laying a solid foundation for advancement within the company.

How hard is it to get an underwriting job?

Securing an underwriting trainee position can be competitive, often requiring a relevant degree such as finance, economics, or business, along with strong analytical skills. Entry-level roles may also require familiarity with industry-specific software and certifications like the Chartered Insurance Professional (CIP) or similar credentials. Candidates with internship experience and good academic records tend to have better chances of obtaining such roles.

What qualifications do I need to be an underwriter?

To become an underwriting trainee, candidates typically need a bachelor's degree in finance, economics, business, or a related field. Strong analytical skills, attention to detail, and proficiency with computer software like Excel are important; some roles may also require relevant certifications such as the Chartered Insurance Underwriter (CIU) or similar credentials.

How do I become an underwriter with no experience?

To become an underwriting trainee with no experience, focus on gaining relevant knowledge through courses in insurance, finance, or risk management. Entry-level roles often require strong analytical skills, attention to detail, and proficiency with computer software; obtaining industry certifications like the Associate in Commercial Underwriting (AU) can also improve your prospects.

What are the key skills and qualifications needed to thrive as an Underwriting Trainee, and why are they important?

To thrive as an Underwriting Trainee, you need strong analytical skills, attention to detail, and a bachelor's degree in finance, business, or a related field. Familiarity with underwriting software, risk assessment tools, and proficiency in Microsoft Excel are typically required, and some employers may value progress toward professional certifications like CPCU. Effective communication, organization, and a willingness to learn help candidates stand out in this entry-level position. These skills and qualities are essential for accurately assessing risks, managing data, and building a successful foundation for a career in insurance underwriting.

What is an underwriting trainee?

An underwriting trainee is an entry-level position in the insurance or financial industry where the individual learns to assess risks, evaluate applications, and determine policy terms under supervision. The role often involves training in underwriting guidelines, using specialized software, and developing analytical skills to support decision-making processes.
What are the most commonly searched types of Underwriting jobs in Springfield, MA? The most popular types of Underwriting jobs in Springfield, MA are:
What are popular job titles related to Underwriting Trainee jobs in Springfield, MA? For Underwriting Trainee jobs in Springfield, MA, the most frequently searched job titles are:
What job categories do people searching Underwriting Trainee jobs in Springfield, MA look for? The top searched job categories for Underwriting Trainee jobs in Springfield, MA are:
What cities near Springfield, MA are hiring for Underwriting Trainee jobs? Cities near Springfield, MA with the most Underwriting Trainee job openings:
Underwriting Trainee jobs near you
Infographic showing various Underwriting Trainee job openings in Springfield, MA as of June 2026, with employment types broken down into 84% Full Time, 15% Part Time, and 1% Contract. Highlights an 98% Physical, 1% Hybrid, and 1% Remote job distribution, with an average salary of $78,602 per year, or $37.8 per hour.
Underwriting Trainee - Small Business Casualty

Underwriting Trainee - Small Business Casualty

CapSpecialty

Hartford, CT • Hybrid

$61K - $87K/yr

Full-time

Life, Retirement, PTO

Posted 7 days ago

Be an early applicant

Job description

This is a hybrid position requiring 3 days in office at our Hartford, CT office location. #LI-Hybrid

At CapSpecialty, we are a specialty underwriting company being driven by well-informed, entrepreneurial and proactive employees. Come join our exciting company where you can really make an impact, and each individual's unique skills and talents are recognized and valued. You will find an accessible leadership team that welcomes opinions and ideas. We owe much of our success to our collaborative environment and set of three guiding principles rooted in customer-centricity, employee excellence and corporate culture.

We offer competitive compensation and benefits packages – including an innovative open vacation plan, generous paid sick and parental leave, fully vested matching 401k, company-paid group term life insurance and short- & long-term disability plans, professional and educational growth opportunities, flexible and casual work environment, and recognition for exceptional performance. Please see our full list of Total Rewards here.

CapSpecialty is seeking college graduates for a year-long Underwriting Trainee position on our new Small Business Casualty Underwriting team. Candidates who successfully complete the program will become Underwriters. As an Underwriting Trainee, the individual will get hands on training within the Small Business Underwriting Unit, in addition to time spent with various department heads and leaders across the company to learn more about insurance operations, the history of CapSpecialty, how insurance companies generate profits and the role of reinsurance. Trainees will learn the basics of how to underwrite specialty lines insurance, analyze financial statements, interpret a policy form and interact with CapSpecialty’s wholesale broker partners. Trainees will participate in department meetings, roundtables, Joint Accountability Groups (JAGs) and large claim meetings as appropriate. Trainees will spend time with Actuarial, Business Development, Claims and Portfolio Management, in addition to accompanying members of the underwriting team on marketing visits. Formal performance evaluations will occur at three, six, nine and 12 months. The Underwriting Training program is designed to provide candidates with the knowledge and skills required to begin a successful underwriting career.

Duties/Responsibilities:

  • Become immersed in the learned insurance principles in order to gain a basic understanding of how to evaluate a risk and an ability to move into a production role upon completion of the Underwriting Training program.
  • Apply underwriting analysis on actual accounts to support production underwriters.
  • Develop relationships with assigned brokers.
  • Perform other duties as needed.

Supervisory Responsibilities:

None.

Core Competencies:

  • Superior oral and written communication skills coupled with sales skills and an ability to develop relationships with brokers.
  • Skilled in the use of personal computers, the internet and multiple software applications and programs.
  • Ability to work independently, problem solve and meet deadlines while also working on a team as a team player.
  • Strong organizational skills with an attention to detail.

Education and Experience:

  • Bachelor’s degree from an accredited college.
  • Previous office experience helpful.

Physical Demands:

  • Prolonged periods of sitting at a desk and working on a computer.
  • May be required to lift up to 10 lbs. at times.
  • May require business travel up to 15%.

CapSpecialty is a leading provider of specialty insurance and bonds for small- to mid-sized businesses in the U.S., offering casualty, professional liability, surety and fidelity products in all 50 states and the District of Columbia. By working with select partners through a limited distribution model, CapSpecialty's creative, hard-working team provides personalized service and cultivates mutually successful partnerships to deliver positive results. CapSpecialty is an operating subsidiary of Berkshire Hathaway, and its carriers have an A+ ("Superior") rating from A.M. Best, writing both admitted and non-admitted policies. For more information, please visit CapSpecialty.com.

Apply today!

Equal Employment Opportunity Employer