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Underwriting Training Program Jobs in Connecticut

Underwriting Manager

Cheshire, CT · Hybrid

$72K - $157K/yr

Coach underwriting leaders, mentor underwriters, and contribute to the design and delivery of underwriting training programs; travel is required. * Makes recommendations on underwriting policy and ...

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Underwriting Training Program information

See Connecticut salary details

$7

$21

$32

How much do underwriting training program jobs pay per hour?

As of Jul 28, 2026, the average hourly pay for underwriting training program in Connecticut is $21.18, according to ZipRecruiter salary data. Most workers in this role earn between $16.01 and $26.06 per hour, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive in the Underwriting Training Program position, and why are they important?

To thrive in an Underwriting Training Program, candidates typically need a bachelor's degree in finance, business, economics, or a related field, along with strong analytical and mathematical skills. Familiarity with spreadsheet software, underwriting systems, and industry certifications such as the Chartered Property Casualty Underwriter (CPCU) can be advantageous. Attention to detail, critical thinking, and effective communication are important soft skills for collaborating with teams and analyzing risk. These abilities help ensure accurate risk assessments, efficient workflow, and a strong foundation for future underwriting responsibilities.

Will AI replace underwriting?

AI is increasingly used in underwriting to automate data analysis and risk assessment, but it is unlikely to fully replace underwriters. Human judgment remains essential for complex cases, decision-making, and interpreting nuanced information. Underwriters will continue to adapt by integrating AI tools into their workflows to improve efficiency and accuracy.

Can I become an underwriter with no experience?

Underwriting training programs often accept candidates with little or no prior experience, as they provide comprehensive training on insurance policies, risk assessment, and industry tools. Having strong analytical skills, attention to detail, and a willingness to learn can help you succeed in entering an underwriting role without previous experience.

What is an Underwriting Training Program job?

An Underwriting Training Program is an entry-level position designed to train individuals in the fundamentals of risk assessment, policy evaluation, and decision-making within the insurance or financial industries. Trainees typically receive structured classroom instruction and hands-on experience working with senior underwriters. The program aims to develop analytical, communication, and decision-making skills necessary for assessing loan or insurance applications. Upon completion, participants often transition into underwriting roles with increased responsibilities.

Is underwriting a high paying career?

Underwriting can be a well-paying career, especially with experience and specialization in areas like commercial or specialty insurance. Salaries vary by industry, location, and level of expertise, but many underwriters earn competitive wages and have opportunities for advancement. Certifications and strong analytical skills can also enhance earning potential.

What can I expect during my time in an Underwriting Training Program?

During an Underwriting Training Program, you can expect to participate in a combination of classroom instruction and hands-on learning, where you’ll be introduced to risk assessment methods, insurance products, and company-specific underwriting guidelines. You’ll often work closely with experienced underwriters, shadowing their activities, reviewing case studies, and gradually taking on more responsibility in evaluating applications. The program typically emphasizes teamwork, ongoing feedback, and regular progress evaluations to prepare you for a full underwriting role. This immersive experience is designed to build your technical knowledge, decision-making skills, and confidence in handling real-world underwriting challenges.

How do you train to be an underwriter?

Training to be an underwriter typically involves completing a relevant degree such as in finance, business, or risk management, followed by on-the-job training where new underwriters learn company-specific policies and tools. Many programs also include coursework or certifications in insurance principles and risk assessment to develop necessary skills.
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Infographic showing various Underwriting Training Program job openings in Connecticut as of July 2026, with employment types broken down into 1% As Needed, 82% Full Time, 13% Part Time, 1% Temporary, and 3% Contract. Highlights an 96% Physical, 1% Hybrid, and 3% Remote job distribution, with an average salary of $44,060 per year, or $21.2 per hour.
Underwriting Trainee - Small Business Casualty

Underwriting Trainee - Small Business Casualty

CapSpecialty, Inc

Hartford, CT • On-site

$61K - $87K/yr

Full-time

Life, Retirement, PTO

Posted 2 days ago


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