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Trainee Insurance Jobs in Connecticut (NOW HIRING)

Granite Group

Sales & Management Trainee

Groton, CT · On-site

The goal of the program is for a Sales and Management Trainee to be ready to take on a sales or ... life insurance, etc.) Earned paid time off totaling 15 days per year as well as paid company ...

Granite Group

Sales & Management Trainee

Hartford, CT · On-site

The goal of the program is for a Sales and Management Trainee to be ready to take on a sales or ... life insurance, etc.) Earned paid time off totaling 15 days per year as well as paid company ...

Hertz

Manager Trainee

Waterbury, CT

$17/hr

We're hiring a Manager Trainee to support location performance, develop leadership skills, and ... Voluntary Insurance Programs - Pet, Legal/Identity Theft, Critical Illness * Perks & Discounts ...

Absolute Roofing

Roofing Inspector Trainee

Monroe, CT · On-site

$450K - $900K/yr

Roofing Inspector Trainee Start your career in roofing sales and learn how to identify storm damage ... Educate homeowners with insurance restoration and complete necessary paperwork Compensation: * Earn ...

Bartlett Tree Experts

Arborist Climber Trainee

Bethel, CT · On-site

$18.50 - $24.25/hr

As an Arborist Climber Trainee, you will be an integral member of a tree care crew working ... Medical, dental, vision, life, and disability insurance * 401k retirement plan * Paid time off and ...

Bartlett Tree Experts

Arborist Climber Trainee

Stamford, CT · On-site

$19.25 - $25/hr

As an Arborist Climber Trainee, you will be an integral member of a tree care crew working ... Medical, dental, vision, life, and disability insurance * 401k retirement plan * Paid time off and ...

Bartlett Tree Experts

Arborist Climber Trainee

Monroe, CT

$18 - $23.25/hr

As an Arborist Climber Trainee, you will be an integral member of a tree care crew working ... Medical, dental, vision, life, and disability insurance * 401k retirement plan * Paid time off and ...

Bartlett Tree Experts

Arborist Climber Trainee

Simsbury, CT · On-site

$18.25 - $23.75/hr

As an Arborist Climber Trainee, you will be an integral member of a tree care crew working ... Medical, dental, vision, life, and disability insurance * 401k retirement plan * Paid time off and ...

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All JobsInsurance JobsTrainee Insurance JobsTrainee Insurance Jobs in Connecticut

Trainee Insurance information

See Connecticut salary details

$24.3K

$41.4K

$60.4K

How much do trainee insurance jobs pay per year?

As of Aug 8, 2026, the average yearly pay for trainee insurance in Connecticut is $41,410.00, according to ZipRecruiter salary data. Most workers in this role earn between $31,400.00 and $48,500.00 per year, depending on experience, location, and employer.

What does a trainee insurance do?

A trainee insurance role typically involves learning the fundamentals of the insurance industry, including understanding different types of insurance policies, risk assessment, and customer service. Trainees often assist senior staff with policy administration, claims processing, and underwriting tasks. The position is designed to provide hands-on experience and training, allowing individuals to develop the skills needed for a successful career in insurance. Over time, trainees may have opportunities to specialize in areas like sales, claims, or underwriting, depending on their interests and company needs.

What are the key skills and qualifications needed to thrive as a trainee insurance professional?

To thrive as a Trainee Insurance professional, you need a basic understanding of insurance principles, analytical skills, and a relevant educational background such as a degree in finance, business, or economics. Familiarity with insurance software, CRM systems, and potentially industry certifications like CII (Chartered Insurance Institute) is advantageous. Strong communication, attention to detail, and a customer-focused mindset are standout soft skills in this role. These abilities are crucial for accurately assessing risk, building client trust, and ensuring efficient and compliant insurance operations.

What are some common challenges faced by trainee insurance professionals during their first year on the job?

Trainee insurance professionals often encounter challenges such as grasping complex policy details, adapting to regulatory requirements, and building effective communication skills with clients. Balancing administrative responsibilities with learning about different insurance products can also be demanding. However, with mentorship and on-the-job training, trainees gradually develop the confidence and expertise needed to succeed in the industry.

What is the difference between Trainee Insurance vs Insurance Agent?

AspectTrainee InsuranceInsurance Agent
Required CredentialsTypically no formal license, on-the-job trainingLicensed, often requires certification
Work EnvironmentTraining programs, supervised learningClient-facing, sales-focused
Employer & Industry UsageInsurance companies, training rolesInsurance agencies, sales roles

In summary, a Trainee Insurance is an entry-level position focused on learning and training within the insurance industry, often without requiring a license. An Insurance Agent, however, is a licensed professional responsible for selling insurance policies and advising clients. The trainee role is a stepping stone toward becoming a licensed insurance agent.

What are the most commonly searched types of Insurance jobs in Connecticut? The most popular types of Insurance jobs in Connecticut are:
What cities in Connecticut are hiring for Trainee Insurance jobs? Cities in Connecticut with the most Trainee Insurance job openings:
Trainee Insurance jobs near you
Infographic showing various Trainee Insurance job openings in Connecticut as of August 2026, with employment types broken down into 1% As Needed, 72% Full Time, 19% Part Time, 3% Temporary, and 5% Contract. Highlights an 90% Physical, 1% Hybrid, and 9% Remote job distribution, with an average salary of $41,410 per year, or $19.9 per hour.

Entry Level Outside Sales Trainee - Northeast

The Reynolds and Reynolds Company

Bridgeport, CT • On-site

$60K/yr

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Re-posted 4 days ago

Reynolds and Reynolds rating

8.4

Company rating: 8.4 out of 10

Based on 46 frontline employees who took The Breakroom Quiz

87th of 242 rated software companies

Job description

Position Description
Reynolds and Reynolds is seeking motivated and hard-working Entry Level Outside Sales Trainees to join our growing team. As an Entry Level Outside Sales Trainee, you will enroll in our 12 month sales training program. This program is comprised of both field based and classroom style training. The classroom training is located at our award winning Reynolds University in Dayton, OH. You will complete courses covering a variety of topics, including dealership operations, sales techniques, and negotiation skills. For the field based sales training, you will be working with your assigned Sales Mentor in their territory, observing the sales process and assisting them on their calls. You will also be given the opportunity to travel with our customer service and installation teams to enhance your knowledge of our products. During the 12 months of training, you can expect to travel, with overnight hotel stays, 80-100% of the time.
Once you complete the training program, you will relocate to an assigned territory and become a Sales Professional. Relocation assistance to this new territory will be provided by the company. You will then be responsible for achieving designated monthly and annual quotas by selling an assigned set of Reynolds products and services. Our products and services are specifically targeted to the automotive industry and include high-end software solutions, marketing services, printed business forms and promotional products. As a Sales Professional, you will sell to both new and existing customers in your assigned territory.
#LI-Remote
Requirements
Must have a valid driver's license, with fewer than 2 moving violations in the last three years and no OVI/DUI/DWI violations in the last five years; Bachelor's degree; Good time management skills; Ability to build strong customer relationships; Excellent oral and written communication skills; Ability to travel (overnight) 80-100% during training; Willing to relocate after successful completion of the training program
Benefits
We strive to offer an environment that provides our associates with the right balance between work and family. We offer a comprehensive benefits package including:
- Medical, dental, vision, life insurance, and a health savings account
- 401(k) with up to 6% matching
- Company car for business and personal use
- Professional development and training
- Promotion from within
- Paid vacation and sick days
- Eight paid holidays
- Referral bonuses
Reynolds and Reynolds promotes a healthy lifestyle by providing a non-smoking environment. Reynolds and Reynolds is an equal opportunity employer.

What Reynolds and Reynolds employees say

Pay

Benefits

Hours and flexibility

Workplace

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About Reynolds and Reynolds

Sourced by ZipRecruiter

Reynolds and Reynolds develops and supports software for automotive retailers. We feature the industry’s only Retail Management System. This platform gives dealers a choice in dealership management systems (DMS) — ERA-IGNITE or POWER — along with retailing tools built to work together to streamline dealership operations and to improve customer satisfaction with the dealership. We also manufacture and distribute business forms and promotional items. Our products help dealers reduce compliance risk, brand their dealership, increase efficiency, and simplify administrative processes. Our associates are the key to our success. We wouldn’t be the leader in the automotive industry without them. We foster an environment that allows associates to grow professionally through engaging work and promotion from within.

Industry

Computer and computer peripheral equipment and software wholesalers

Company size

1,001 - 5,000 Employees

Headquarters location

Dayton, OH, US

Year founded

1866

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