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Trainee Insurance Jobs in Boston, MA (NOW HIRING)

84 Lumber Company

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 ...

84 Lumber Company

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 ...

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

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 ...

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

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 ...

Veolia Environnement SA

O&M Technician Trainee

Lynn, MA · On-site

$33.62/hr

The trainee will work closely with experienced technicians to learn the necessary skills and ... insurance; retirement plans, savings accounts; tuition reimbursement; paid volunteering and more.

Veolia Environnement SA

O&M Technician Trainee

Lynn, MA · On-site

$33.62/hr

The trainee will work closely with experienced technicians to learn the necessary skills and ... insurance; retirement plans, savings accounts; tuition reimbursement; paid volunteering and more.

Veolia

O&M Technician Trainee

Lynn, MA · On-site

The trainee will work closely with experienced technicians to learn the necessary skills and ... insurance; retirement plans, savings accounts; tuition reimbursement; paid volunteering and more.

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 Your Future. Lead the Business. The RISE Program is designed to accelerate high-potential early ...

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 ...

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Showing results 1-20

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 Aug 27, 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 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 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 August 2026, with employment types broken down into 96% Full Time, and 4% Part Time. Highlights an 93% In-person, 3% Hybrid, and 4% Remote job distribution, with an average salary of $47,292 per year, or $22.7 per hour.

Insurance Operations Trainee

SAFETY INSURANCE COMPANY

Boston, MA • Hybrid

Full-time

Medical, Dental, Vision, Retirement, PTO

Posted yesterday

New

Safety Insurance rating

7.8

Company rating: 7.8 out of 10

Based on 5 frontline employees who took The Breakroom Quiz

195th of 312 rated insurance

Job description

Benefits of Working for Safety

Safety Insurance is proud to be one of the leading property and casualty insurance providers in Massachusetts. We are committed to supporting independent agents and their customers through our unwavering dedication to excellence. Our success is built on a simple philosophy: deliver the highest quality insurance products at competitive rates while providing exceptional service at every step.

At Safety Insurance, we don't just offer jobs - we offer careers that are challenging, fulfilling, and designed to grow with you.

Our people are our greatest asset. A diverse workforce makes us stronger, more innovative, and better equipped to serve our customers. At Safety, we empower our employees to be their best by fostering an inclusive environment and offering resources that support their careers, education, and families. We also understand the importance of work-life balance. That's why we offer hybrid work options, flexible schedules, and a 37.5-hour workweek. Conveniently located in the heart of Boston's financial district, our downtown office is a positive space where employees can stay connected to both each other and the pulse of the city.

Safety's benefits go beyond the basics. In addition to competitive salaries, our comprehensive benefits package includes:

  • 3 weeks accrued paid time off +paid holidays each year
  • Health insurance (medical, dental, vision)
  • Annual 401(k) Employer Contribution (up to 8% of your base salary)
  • 100% tuition reimbursement
  • Free on-site fitness center
  • Complimentary coffee and breakfast service
  • Hybrid work schedules
  • Working Advantage Discount Program
  • Employee Assistance Program
  • ...and much more!

Job Summary

This position will consist of training for Personal and Commercial Lines of Insurance. Training will be comprised of both policy and system comprehension. Training will also consist of working on projects for various departments. This position will prepare trainees to apply for open positions within Underwriting and Insurance Operations, which includes Personal and Commercial Lines Underwriting, Products and Services, Service Center, Customer Engagement and Billing. This position has an in-office requirement 5 days a week at our Boston, MA location.

Responsibilities

  • Provides support for all operations within the Insurance Operations and Underwriting Departments as needed.

  • Verifies data through various internal and external systems to ensure accurate policy information.

  • Compiles data to support the appropriate departments' efforts to eliminate policy errors.

  • Notifies Agencies of policy changes or errors.

  • Reviews new business applications for accuracy, communicating any issues to Underwriting staff.

  • Processes endorsements within required time frame.

  • Performs other activities and special projects as required.

  • College degree required.

  • Commitment to providing excellent customer service to agents and policyholders.

  • Ability to work both independently and within a team environment.

  • Excellent verbal and written communication skills required.

  • Strong working knowledge of Excel, Outlook, Word and Access.

  • Detail oriented, able to plan and multitask effectively.

  • Ability to understand difficult problems and provide solutions.

What Safety Insurance employees say

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