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Trainee Insurance Jobs in Portland, CT (NOW HIRING)

Manager Trainee

Plainville, CT · On-site

$47K - $51K/yr

Medical, dental and vision insurance * Holiday pay * Flexible Spending Accounts (FSA) for medical ... The Manager Trainee is a full-time, entry-level position designed to prepare you for a leadership ...

Manager Trainee

Plainville, CT · On-site

$47K - $51K/yr

Medical, dental and vision insurance * Holiday pay * Flexible Spending Accounts (FSA) for medical ... The Manager Trainee is a full-time, entry-level position designed to prepare you for a leadership ...

The Management Trainee will work closely with experienced managers to learn about Outside Sales ... and AD&D Insurance, 100% Company Paid • Paid Time Off and Holidays • Skills Development ...

The Management Trainee will work closely with experienced managers to learn about Outside Sales ... AD&D Insurance, 100% Company Paid Paid Time Off and Holidays Skills Development, Training and ...

Underwriting Trainee

Hartford, CT · On-site

$65K - $75K/yr

Draft POSITION SUMMARY The Underwriter Trainee ("Trainee") participates in the commercial ... Supporting the Companies' underwriters in developing insurance solutions for a wide range of small ...

Our Sales Trainees are exposed to all areas of our business and are given the opportunity to ... Life Insurance coverage for you and options for your family. * Save on expenses with Flexible ...

Sales Trainee

Wallingford, CT · On-site

$20 - $24/hr

Our Sales Trainees are exposed to all areas of our business and are given the opportunity to ... Life Insurance coverage for you and options for your family. * Save on expenses with Flexible ...

Arborist Climber Trainee

Simsbury, CT

$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 ...

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 ...

Account Manager Trainee

Hartford, CT · On-site

$51K - $53K/yr

What's In It for You Our Account Manager Trainees earn between $51,000 - $53,000 base with an 11.5% ... You'll get great benefits including Medical and Dental insurance, generous Paid Time Off (including ...

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Showing results 1-20

Trainee Insurance information

See Portland, CT salary details

$25.8K

$44.1K

$64.3K

How much do trainee insurance jobs pay per year?

As of Aug 26, 2026, the average yearly pay for trainee insurance in Portland, CT is $44,078.00, according to ZipRecruiter salary data. Most workers in this role earn between $33,400.00 and $51,600.00 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 Portland, CT?

The most popular types of Insurance jobs in Portland, CT are:

What cities near Portland, CT are hiring for Trainee Insurance jobs?

Cities near Portland, CT with the most Trainee Insurance job openings:

Infographic showing various Trainee Insurance job openings in Portland, CT as of August 2026, with employment types broken down into 1% As Needed, 73% Full Time, 20% Part Time, and 6% Contract. Highlights an 85% Physical, 1% Hybrid, and 14% Remote job distribution, with an average salary of $44,078 per year, or $21.2 per hour.

Remote Leadership Trainee

Mansfield, CT • Remote

Fisher Agencies
Insurance Services • 11 - 50 employees

Full-time

Life

Re-posted 25 days ago


Job description

Fisher Agencies is seeking enthusiastic and driven individuals for the role of Remote Leadership Trainee. This entry-level position offers a unique opportunity to develop leadership skills through comprehensive training and mentorship, all while working remotely.

As a Remote Leadership Trainee, you will engage with team members, assist in daily operations, and learn key strategies to lead and motivate teams effectively. This role is ideal for those looking to begin a career in leadership within a supportive and dynamic environment.

Join us at Fisher Agencies and start your journey toward becoming a successful leader with excellent growth prospects.

Requirements

  • Strong communication and interpersonal skills
  • Self-motivated and eager to learn
  • Positive attitude with a willingness to take initiative
  • Ability to work independently in a remote setting
  • Basic proficiency with computer applications and virtual communication tools
  • Previous experience in sales, customer service, or leadership is a plus but not required

Benefits

  • Training & Development
  • Work From Home
  • Life Insurance (Basic, Voluntary & AD&D)