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Trainee Insurance Jobs in Connecticut (NOW HIRING)

Charles IT

IT Trainee

Middletown, CT

We are excited to welcome a new class of trainees to our exceptional team in November 2026 ... insurance, paid holidays, PTO, 401(k), and performance-based bonuses. Team members also enjoy ...

Charles IT

IT Trainee

Middletown, CT · On-site

We are excited to welcome a new class of trainees to our exceptional team in November 2026 ... insurance, paid holidays, PTO, 401(k), and performance-based bonuses. Team members also enjoy ...

Ameriprise Financial

Financial Advisor Trainee

Greenwich, CT · On-site

$47K - $58K/yr

... Advisor Trainee to grow with us. We're offering more than just a job - this is a career track ... Series 7 & 66 Exams and state Insurance license will be required within first 6 months of hire.

Bartlett Tree Experts

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 ...

Bartlett Tree Experts

Arborist Climber Trainee

New Milford, CT · On-site

$18.75 - $24.50/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

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 ...

Bartlett Tree Experts

Arborist Climber Trainee

Monroe, CT · On-site

$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

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 · On-site

$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

New Milford, CT · On-site

$18.75 - $24.50/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

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

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 ...

HILTI

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 41-60

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 Sep 5, 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, 2% Temporary, and 6% Contract. Highlights an 89% Physical, 1% Hybrid, and 10% Remote job distribution, with an average salary of $41,410 per year, or $19.9 per hour.

IT Trainee

Charles IT

Middletown, CT

Temporary

Medical, Dental, Vision, Life, Retirement, PTO

Posted 4 days ago

Job description

Exceptional Service, Endless Improvement, Passionate People, and Honest and Forthright. Guided by our values, we foster a culture of growth, balance, and belonging where every team member can thrive.  

We are excited to welcome a new class of trainees to our exceptional team in November 2026! Participate in our 12-week, in-house IT Trainee Program, designed to provide hands-on experience in: 

  • Our customer service approach 
  • Active Directory user and group management 
  • Printer and peripheral installations 
  • New desktop setups 
  • Office 365 administration 
  • Basic server maintenance and administration 
  • Customer network audits 
  • First-level security incidents (phishing, SPAM, Dark Web alerts) 
  • Responding to client tickets via phone and email 
  • Other duties as assigned

Responsibilities 

  • Support administrative and general office tasks 
  • Assist with IT services and projects, including on-site deliveries and equipment drop-offs 
  • Help maintain an organized office environment and support team efficiency 
  • Learn and navigate our ticketing system, a key part of our business operations 
  • Complete self-paced technical training modules and certifications 

Requirements

  • Availability to work full-time (40 hours per week) for the full 12-week program 
  • Associate, Bachelor's, or Graduate degree in Information Technology, or equivalent hands-on experience, is a plus  
  • Technical certifications such as CompTIA Server+, Security+, Network+, or Microsoft certifications (MS-900, SC-900, AZ-900) is a plus  
  • Prior experience in a help desk or related IT environment is a plus 
  • Strong motivation to learn and advance professionally 
  • Excellent organizational, time management, analytical, and problem-solving skills 
  • Clear written and verbal communication abilities 
  • Proficiency in Microsoft Office 
  • Must be 18 years of age or older 
  • Must have unrestricted authorization to work in the U.S.
  • Essential Functions include the ability to occasionally lift and carry items weighing up to 30 pounds, as well as perform tasks involving standing, walking, bending, reaching, pushing, pulling, and moving office equipment, boxes, supplies, and other materials. Some physical activity may be involved during office moves, deliveries, workspace setup, and other projects as needed.

Benefits

  • Paid internship 
  • Paid training and certifications 
  • Weekly check-ins to track progress and provide mentorship 
  • Small class size (5-6 participants) for personalized support 
  • Opportunity for a full-time role as a Desktop Support Specialist upon successful completion of the program 

Charles IT offers a comprehensive benefits package, including medical, dental, vision, life and disability insurance, paid holidays, PTO, 401(k), and performance-based bonuses. Team members also enjoy ongoing training, professional development, quarterly team-building events, and a collaborative workplace culture.   

Commitment to Inclusion:   

Charles IT is an equal opportunity employer committed to fostering an inclusive and respectful work environment. We welcome diverse backgrounds and perspectives and do not discriminate based on any protected characteristic.

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