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Trainee Insurance Jobs in Ontario (NOW HIRING)

Cintas

Management Trainee

Windsor, ON

CA$61K/yr

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

Cintas

Management Trainee

Toronto, ON · On-site

CA$64K/yr

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

Cintas

Management Trainee

Cambridge, ON · On-site

CA$61K/yr

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

Cintas

Management Trainee

Cambridge, ON · On-site

CA$61K/yr

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

Cintas

Management Trainee

Toronto, ON · On-site

CA$64K/yr

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

Halfords

Trainee Tyre Technician Apply now Job no: 566841 Work type: Full time Site: Thurso Categories ... Discounts on everything from groceries, shopping, insurance, days out, restaurants and more

Halfords

Trainee Tyre Technician - Inverness Apply now Job no: 565959 Work type: Full time Site: Inverness ... Discounts on everything from groceries, shopping, insurance, days out, restaurants and more

Enterprise Holdings

Management Trainee

Pembroke, ON

CA$54K/yr

Life Insurance; Prescription coverage * Employee discounts on car rentals, car purchases and much ... that our Management Trainee position does not typically fall under an eligible National ...

Enterprise Holdings

Management Trainee

Thunder Bay, ON · On-site

CA$51K/yr

Life Insurance; Prescription coverage * Employee discounts on car rentals, car purchases and much ... that our Management Trainee position does not typically fall under an eligible National ...

Enterprise Holdings

Management Trainee

Pembroke, ON · On-site

CA$54K/yr

Life Insurance; Prescription coverage * Employee discounts on car rentals, car purchases and much ... that our Management Trainee position does not typically fall under an eligible National ...

Enterprise Holdings

Management Trainee

North Bay, ON · On-site

CA$54K/yr

Life Insurance; Prescription coverage * Employee discounts on car rentals, car purchases and much ... that our Management Trainee position does not typically fall under an eligible National ...

Enterprise Holdings

Management Trainee

Guelph, ON · On-site

CA$53K/yr

Life Insurance; Prescription coverage * Employee discounts on car rentals, car purchases and much ... that our Management Trainee position does not typically fall under an eligible National ...

Enterprise Holdings

Management Trainee

Toronto, ON

CA$55K/yr

Life Insurance; Prescription coverage * Employee discounts on car rentals, car purchases and much ... that our Management Trainee position does not typically fall under an eligible National ...

Enterprise Holdings

Management Trainee

Kitchener, ON · On-site

CA$53K/yr

Life Insurance; Prescription coverage * Employee discounts on car rentals, car purchases and much ... that our Management Trainee position does not typically fall under an eligible National ...

Enterprise Holdings

Management Trainee

Woodstock, ON

CA$53K/yr

Life Insurance; Prescription coverage * Employee discounts on car rentals, car purchases and much ... that our Management Trainee position does not typically fall under an eligible National ...

Enterprise Holdings

Management Trainee

Midland, ON · On-site

CA$55K/yr

Life Insurance; Prescription coverage * Employee discounts on car rentals, car purchases and much ... that our Management Trainee position does not typically fall under an eligible National ...

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All JobsInsurance JobsTrainee Insurance JobsTrainee Insurance Jobs in Ontario

Trainee Insurance information

See Ontario salary details

$18K

$42.4K

$78.5K

How much do trainee insurance jobs pay per year?

As of Aug 22, 2026, the average yearly pay for trainee insurance in Ontario is $42,430.00, according to ZipRecruiter salary data. Most workers in this role earn between $32,500.00 and $45,500.00 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 Ontario?

The most popular types of Insurance jobs in Ontario are:

Trainee Insurance jobs near you
Infographic showing various Trainee Insurance job openings in Ontario as of August 2026, with employment types broken down into 1% As Needed, 68% Full Time, 27% Part Time, and 4% Contract. Highlights an 89% Physical, 1% Hybrid, and 10% Remote job distribution, with an average salary of $42,430 per year, or $20.4 per hour.

Trainee Service Representative - Insurance

All-Risks Insurance Brokers - Steels Corners

Thornhill, ON • On-site

Part-time

PTO

Posted yesterday

New

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Job description

About the Role

The Trainee Service Representative will provide administrative and technical support to our brokers and service team.

This is primarily a behind-the-scenes role with no direct client interaction. You will work with insurance information, policy documentation, brokerage systems, and internal processes while developing your insurance knowledge and professional skills.

Key Responsibilities

  • Provide administrative and technical support to brokers and service representatives.
  • Enter, update, and maintain accurate information in brokerage management systems.
  • Process, organize, and review insurance documentation and policy information.
  • Review policy details, coverage, endorsements, and other insurance information for accuracy.
  • Assist with comparing coverage options and information from different insurance markets.
  • Identify missing information, inconsistencies, and potential coverage gaps for review by experienced brokers.
  • Perform data entry and administrative tasks with a high degree of accuracy.
  • Learn and efficiently use insurance and brokerage software systems.
  • Assist with research, documentation, and other tasks as assigned.
  • Maintain confidentiality and handle insurance information in a professional and ethical manner.

What We're Looking For

Insurance & Technical Skills

  • RIBO licence is not required.
  • Willingness to obtain a RIBO licence is considered a strong asset.
  • Strong interest in learning the insurance industry.
  • Strong insurance acumen or the ability to quickly understand and apply insurance concepts.
  • Excellent computer skills and ability to learn new software quickly.
  • Comfortable working with multiple applications and systems.

Analytical & Problem-Solving Skills

  • Excellent active listening, analytical, and comprehension skills.
  • Strong critical-thinking and problem-solving abilities.
  • Ability to understand and compare insurance coverage options.
  • Ability to recognize inconsistencies and potential gaps in coverage.
  • Strong attention to detail and accuracy.
  • Ability to understand complex insurance situations and information.

Communication & Professional Skills

  • Excellent written and verbal communication skills.
  • Confident, professional, and clear communication.
  • Strong organizational skills and ability to manage multiple priorities.
  • Comfortable working independently and taking initiative.
  • Strong work ethic and commitment to quality.
  • Professional, dependable, and ethical.
  • Self-motivated, driven, ambitious, and eager to learn.
  • Positive attitude and willingness to continuously develop new skills.

What We Offer

  • Part-time or full-time opportunity
  • Comprehensive hands-on training
  • Support and mentorship from experienced insurance professionals
  • Opportunity to develop strong insurance and brokerage knowledge
  • Opportunity to pursue RIBO licensing
  • Professional and supportive team environment
  • Long-term career growth opportunities within an established insurance organization

Who We're Looking For

This role is ideal for someone who is highly comfortable with computers, naturally analytical, detail-oriented, organized, and eager to learn.

You don't need to be an experienced insurance professional. We are looking for someone with the right attitude, work ethic, intelligence, and willingness to learn who can develop into a strong insurance professional over time.

If you enjoy working with information, solving problems, understanding complex concepts, and getting the details right, we want to hear from you.

Apply Today

Please submit your resume for consideration.

We thank all applicants for their interest; however, only candidates selected for an interview will be contacted.

All-Risks Insurance Brokers Ltd. is an equal opportunity employer and is committed to providing accommodations throughout the recruitment process in accordance with the AODA. Accommodations are available upon request.