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Underwriter Trainee Jobs in Springfield, MA (NOW HIRING)

Cyber and Tech Risk UW SR

Hartford, CT · On-site

$99K - $117K/yr

We combine underwriting expertise, cyber risk intelligence, and advanced analytics to help organizations anticipate, prevent, and mitigate evolving digital threats. Our cyber offerings are supported ...

Cyber and Tech Risk UW SR

Hartford, CT · On-site +1

$99K - $117K/yr

We combine underwriting expertise, cyber risk intelligence, and advanced analytics to help organizations anticipate, prevent, and mitigate evolving digital threats. Our cyber offerings are supported ...

Cyber and Tech Risk UW SR

Hartford, CT · On-site

$99K - $117K/yr

We combine underwriting expertise, cyber risk intelligence, and advanced analytics to help organizations anticipate, prevent, and mitigate evolving digital threats. Our cyber offerings are supported ...

This role partners closely with underwriting, product, actuarial, and technology leaders to deliver scalable, production ready models and AI driven decision systems that support complex risks ...

Showing results 41-53

Underwriter Trainee information

See Springfield, MA salary details

$31.6K

$76.8K

$135.8K

How much do underwriter trainee jobs pay per year?

As of Aug 9, 2026, the average yearly pay for underwriter trainee in Springfield, MA is $76,771.00, according to ZipRecruiter salary data. Most workers in this role earn between $59,400.00 and $84,700.00 per year, depending on experience, location, and employer.

How much does an underwriter trainee earn?

An underwriter trainee typically earns between $40,000 and $55,000 annually, depending on location, industry, and experience. Entry-level positions may start lower, but with training and skill development, salaries can increase as they gain underwriting knowledge and certifications.

How much do beginner underwriters make?

Entry-level underwriters typically earn between $45,000 and $60,000 annually, depending on location and industry. Starting salaries may increase with relevant certifications, such as the Chartered Property Casualty Underwriter (CPCU), and experience with underwriting software and risk assessment. Compensation can also vary based on the employer and the complexity of the policies handled.

What are the key skills and qualifications needed to thrive as an underwriter trainee?

To thrive as an Underwriter Trainee, you need strong analytical abilities, 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 Excel are commonly required, and industry certifications like CPCU can be advantageous. Excellent communication, problem-solving, and organizational skills help you collaborate with stakeholders and manage multiple priorities. These skills are essential to accurately assess risk, make informed decisions, and contribute to the overall profitability and integrity of the insurance company.

What is the difference between Underwriter Trainee vs Underwriter?

AspectUnderwriter TraineeUnderwriter
Required CredentialsBachelor's degree, training programsExperience, certifications like CPCU or ARM often preferred
Work EnvironmentTraining programs, supervised tasksIndependent decision-making, client interaction
Employer & Industry UsageInsurance companies, entry-level rolesInsurance companies, experienced roles
Search & Comparison IntentLearning about entry-level underwriting rolesUnderstanding experienced underwriting positions

The main difference between an Underwriter Trainee and an Underwriter is experience level. Trainees are in training, focusing on learning the basics, while Underwriters have gained experience and handle complex risk assessments independently.

What is an underwriter trainee?

An Underwriter Trainee is an entry-level professional who learns how to evaluate risks and determine appropriate insurance coverage and premiums under the supervision of experienced underwriters. Their training involves learning about insurance policies, analyzing applications, assessing potential risks, and making recommendations based on company guidelines. This role serves as a starting point for a career in underwriting, providing foundational knowledge and practical experience in the insurance industry.

What are some typical challenges an underwriter trainee might encounter during their first year on the job?

As an Underwriter Trainee, one common challenge is learning to balance risk assessment with client needs, while adhering to company policies and regulatory requirements. Trainees often need to quickly develop a strong understanding of underwriting guidelines and how to apply them to real-world cases, which can be complex and varied. Additionally, adapting to a fast-paced environment and effectively collaborating with senior underwriters, brokers, and agents requires strong communication and organizational skills. Overcoming these challenges is an important part of gaining confidence and proficiency in the role.

How do I become an underwriter trainee with no experience?

To become an underwriter trainee with no experience, candidates typically need a high school diploma or equivalent; some employers prefer or require a bachelor's degree in fields like finance, business, or economics. Entry-level positions often provide on-the-job training, and developing skills in analysis, attention to detail, and familiarity with underwriting software can improve chances. Certifications such as the Associate in Commercial Underwriting (ACU) or similar can also enhance prospects for advancement.
What are the most commonly searched types of Underwriter jobs in Springfield, MA? The most popular types of Underwriter jobs in Springfield, MA are:
What are popular job titles related to Underwriter Trainee jobs in Springfield, MA? For Underwriter Trainee jobs in Springfield, MA, the most frequently searched job titles are:
What job categories do people searching Underwriter Trainee jobs in Springfield, MA look for? The top searched job categories for Underwriter Trainee jobs in Springfield, MA are:
What cities near Springfield, MA are hiring for Underwriter Trainee jobs? Cities near Springfield, MA with the most Underwriter Trainee job openings:
Infographic showing various Underwriter Trainee job openings in Springfield, MA as of August 2026, with employment types broken down into 93% Full Time, 6% Part Time, and 1% Contract. Highlights an 86% Physical, 1% Hybrid, and 13% Remote job distribution, with an average salary of $76,771 per year, or $36.9 per hour.

Account Executive Officer/Sr. Underwriter, Specialty Group Captives

Travelers

Hartford, CT • On-site

$114K - $189K/yr

Full-time

Medical, Life, Retirement, PTO

Re-posted 2 days ago


Travelers Insurance rating

8.9

Company rating: 8.9 out of 10

Based on 175 frontline employees who took The Breakroom Quiz

48th of 304 rated insurance


Job description

Who Are We?

Taking care of our customers, our communities and each other. That’s the Travelers Promise. By honoring this commitment, we have maintained our reputation as one of the best property casualty insurers in the industry for over 170 years. Join us to discover a culture that is rooted in innovation and thrives on collaboration. Imagine loving what you do and where you do it.

Compensation Overview

The annual base salary range provided for this position is a nationwide market range and represents a broad range of salaries for this role across the country. The actual salary for this position will be determined by a number of factors, including the scope, complexity and location of the role; the skills, education, training, credentials and experience of the candidate; and other conditions of employment. As part of our comprehensive compensation and benefits program, employees are also eligible for performance-based cash incentive awards.

Salary Range

$114,700.00 - $189,200.00

Target Openings

1

What Is the Opportunity?

Specialty Group Captives (SGC) is an important and growing segment within National Accounts. SGC offers loss responsive programs to larger middle market clients that desire a more holistic approach to risk management than traditional guaranteed cost insurance.
Our current portfolio consists of 16 programs and $250M of written premium. We launched two new group captives one for construction risks in 2024 and one for middle market risks in 2025.
SGC underwrites some of the most complex program structures within the Travelers enterprise. If you're looking to grow your underwriting development or simply want a greater challenge, this may be the opportunity you're looking for. We are growing and we need smart, enthusiastic, detail oriented and outgoing individuals as we continue to grow Travelers footprint farther into the group captive market.

What Will You Do?

  • Responsible for the profitability , growth and retention of an assigned book of business. The average AEO is responsible for 3-4 captive programs per year. The programs range in size and complexity from 12 to 1,300 insured and up to $100M in premiums.
  • Underwrite and skillfully negotiate complex customer accounts to minimize risk and maximize profitability.
  • Develop and maintain relationships with internal partners within the business unit and across the enterprise to create sales plans and identify cross-selling opportunities.
  • Identify and capture new business opportunities using consultative marketing and sales skills.
  • Independently develop and execute agency sales plans and frequently partner with your Managing Director (MD) to develop region/group sales plans.
  • May assist in the training and mentoring of less experienced Account Executives.
  • Travel nationally and internationally required on occasion.
  • Perform other duties as assigned.

What Will Our Ideal Candidate Have?

  • Bachelor’s degree.
  • Six to eight years of relevant underwriting experience with experience in commercial lines.
  • Deep knowledge of underwriting commercial lines products, the regulatory environment, and the broader insurance market.
  • Strong critical thinking skills with the ability to proactively identify underwriting, marketing, or financial challenges and analyze available information to make timely decisions in alignment with our risk appetite.
  • Excellent communication skills with the ability to successfully negotiate in difficult situations with agents and brokers.
  • CPCU designation.

What is a Must Have?

  • Four years of underwriting, claim, operations, risk assessment, actuarial, sales, product, or finance experience.

What Is in It for You?

  • Health Insurance: Employees and their eligible family members – including spouses, domestic partners, and children – are eligible for coverage from the first day of employment.
  • Retirement: Travelers matches your 401(k) contributions dollar-for-dollar up to your first 5% of eligible pay, subject to an annual maximum. If you have student loan debt, you can enroll in the Paying it Forward Savings Program. When you make a payment toward your student loan, Travelers will make an annual contribution into your 401(k) account. You are also eligible for a Pension Plan that is 100% funded by Travelers.
  • Paid Time Off: Start your career at Travelers with a minimum of 20 days Paid Time Off annually, plus nine paid company Holidays.
  • Wellness Program: The Travelers wellness program is comprised of tools, discounts and resources that empower you to achieve your wellness goals and caregiving needs. In addition, our mental health program provides access to free professional counseling services, health coaching and other resources to support your daily life needs.
  • Volunteer Encouragement: We have a deep commitment to the communities we serve and encourage our employees to get involved. Travelers has a Matching Gift and Volunteer Rewards program that enables you to give back to the charity of your choice.

Employment Practices

Travelers is an equal opportunity employer. We value the unique abilities and talents each individual brings to our organization and recognize that we benefit in numerous ways from our differences. 

In accordance with local law, candidates seeking employment in Colorado are not required to disclose dates of attendance at or graduation from educational institutions.

If you are a candidate and have specific questions regarding the physical requirements of this role, please send us an email so we may assist you.

Travelers reserves the right to fill this position at a level above or below the level included in this posting.

To learn more about our comprehensive benefit programs please visit http://careers.travelers.com/life-at-travelers/benefits/.


What Travelers Insurance employees say

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About Travelers

Sourced by ZipRecruiter

We are an insurance company that cares. Travelers takes on the risk and provides the coverage you need to protect the things that are important to you — your home, your car, your valuables and your business — so you don’t have to worry. We have been around for more than 165 years and have earned a reputation as one of the best property casualty insurers in the industry because we take care of our customers. Our expertise and focus on innovation have made us a leader in personal, business and specialty insurance and the only property casualty company in the Dow Jones Industrial Average. Every day, our approximately 30,000 employees and 13,500 independent agents and brokers in the United States, Canada, the United Kingdom and Ireland help provide peace of mind to our customers.

Industry

Insurance services

Company size

10,000+ Employees

Headquarters location

New York, NY, US

Year founded

1853