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Trainee Insurance Jobs in Boston, MA (NOW HIRING)

PDS Health

Operations Manager Trainee

Chelmsford, MA · On-site

In lieu of a valid driver's license and automobile insurance, Operations Manager Trainee must have reliable means of alternate transportation which would allow for required, timely travel to multiple ...

PDS Health

Operations Manager Trainee

Waltham, MA · On-site

In lieu of a valid driver's license and automobile insurance, Operations Manager Trainee must have reliable means of alternate transportation which would allow for required, timely travel to multiple ...

PDS Health

Operations Manager Trainee

West Roxbury, MA · On-site

In lieu of a valid driver's license and automobile insurance, Operations Manager Trainee must have reliable means of alternate transportation which would allow for required, timely travel to multiple ...

PDS Health

Operations Manager Trainee

Waltham, MA · On-site

$30.50/hr

In lieu of a valid driver's license and automobile insurance, Operations Manager Trainee must have reliable means of alternate transportation which would allow for required, timely travel to multiple ...

PDS Health

Operations Manager Trainee

Burlington, MA · On-site

In lieu of a valid driver's license and automobile insurance, Operations Manager Trainee must have reliable means of alternate transportation which would allow for required, timely travel to multiple ...

PDS Health

Operations Manager Trainee

West Roxbury, MA · On-site

$31.75/hr

In lieu of a valid driver's license and automobile insurance, Operations Manager Trainee must have reliable means of alternate transportation which would allow for required, timely travel to multiple ...

PDS Health

Operations Manager Trainee

Chelmsford, MA · On-site

$30.50/hr

In lieu of a valid driver's license and automobile insurance, Operations Manager Trainee must have reliable means of alternate transportation which would allow for required, timely travel to multiple ...

84 Lumber Company

Full-Time Manager Trainee

Holbrook, MA · 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 ...

Red Bull

Sales Trainee

Wilmington, MA

$25 - $27/hr

Company Description This is a training role that is made to prepare the Sales Trainee for the ... Insurance, Tuition Reimbursement (Benefits listed may vary depending on the nature of your ...

84 Lumber Company

Full-Time Manager Trainee

Holbrook, MA

$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 ...

Graybar

Sales Trainee

Westwood, MA · On-site

$24.04/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 ...

Tawa Supermarket Inc

Management Trainee

Quincy, MA · On-site

$19 - $28/hr

Management Trainee (MT) for RISE ProgramRISE Program -- Retail Immersion & Store Excellence Build ... Medical, Vision, Dental, and Life Insurance * 401(k) Plan with Company Match * Paid Time Off

Ruby Wines Inc

Sales trainee/Merchandiser

Avon, MA · On-site

$18.25 - $20.50/hr

Description: SALES TRAINEE/MERCHANDISER GREATER BOSTON AREA RUBY WINES INC. We are seeking a ... Additional Information: · Health/Dental Insurance · Life insurance · 401K plan · Profit Shari

Graybar

Sales Trainee

Westwood, MA · On-site

$24.04/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 ...

Geico

Auto Damage Trainee (Field)

Boston, MA

Your Impact at GEICO As a FieldAuto Damage Trainee,you'llprovide reassurance and solutions that ... Consult with involved parties, review insurance contracts, inspect vehicles, write estimates, and ...

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All JobsInsurance JobsTrainee Insurance JobsTrainee Insurance Jobs in Boston, MA

Trainee Insurance information

See Boston, MA salary details

$27.7K

$47.3K

$69K

How much do trainee insurance jobs pay per year?

As of Jul 28, 2026, the average yearly pay for trainee insurance in Boston, MA is $47,292.00, according to ZipRecruiter salary data. Most workers in this role earn between $35,900.00 and $55,400.00 per year, depending on experience, location, and employer.

What does a trainee insurance role involve?

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, and why are they important?

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 Boston, MA? The most popular types of Insurance jobs in Boston, MA are:
Trainee Insurance jobs near you
Infographic showing various Trainee Insurance job openings in Boston, MA as of July 2026, with employment types broken down into 96% Full Time, and 4% Part Time. Highlights an 96% In-person, and 4% Remote job distribution, with an average salary of $47,292 per year, or $22.7 per hour.
Remote Leadership Trainee

Remote Leadership Trainee

Fisher Agencies

Boston, MA • On-site, Remote

Full-time

Life

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)

Apply