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Trainee Insurance Jobs in Ontario (NOW HIRING)

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 ...

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 ...

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 ...

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 ...

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 ...

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

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 ...

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 ...

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 ...

Management Trainee

London, 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 ...

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 ...

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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Showing results 1-20

Trainee Insurance information

See Ontario salary details

$18K

$42.4K

$78.5K

How much do trainee insurance jobs pay per year?

As of Aug 9, 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:
Infographic showing various Trainee Insurance job openings in Ontario as of August 2026, with employment types broken down into 87% Full Time, and 13% Part Time. Highlights an 100% In-person job distribution, with an average salary of $42,430 per year, or $20.4 per hour.

Insurance Account Representative Trainee

Matthew Jeninga - Desjardins Agent Intern

Oshawa, ON

CA$45K/yr

Full-time, Contractor

Re-posted 3 days ago


Job description

Insurance Account Representative

Desjardins Insurance Agency

Location: Oshawa, ON
Employment Type: Full-Time
Hours: 35 Hours Per Week
Training Compensation: $45,000 Annualized

Launch Your Career with Desjardins Insurance

Are you energetic, customer-focused, and ready to build a rewarding career in the insurance industry?

Our Desjardins Insurance Agency is seeking motivated individuals to join our team as Insurance Account
Representative Trainees in a fully paid 3-month training program. Through structured learning, hands-on
experience, mentorship, and personalized coaching, you will develop the skills, knowledge, and confidence
needed to succeed in a client-focused insurance role.

This opportunity is ideal for individuals who enjoy helping people, building relationships, and growing
professionally in a supportive and team-oriented environment.

Successful trainees will have the opportunity to transition into a permanent full-time Insurance Account
Representative position, providing a clear pathway to a long-term and rewarding career with our agency.

What You'll Do

• Participate fully in training sessions focused on Desjardins products and services, client service excellence,
sales and relationship-building techniques, and agency operations and processes.
• Provide professional customer service to existing and prospective clients in person and over the phone.
• Assist with policy inquiries, servicing, appointment scheduling, client follow-up activities, and administrative
support.
• Learn to identify client needs and recommend appropriate insurance solutions.
• Maintain accurate client records and support daily agency operations.
• Meet training milestones while embracing coaching, feedback, and continuous learning.

Who We’re Looking For

Preferred Qualifications
• Experience in client service, retail, hospitality, sales, banking, or office administration.
• High school diploma or equivalent; post-secondary education is an asset.
• Basic computer proficiency including Microsoft Office and web-based applications.
• Insurance or financial services experience is an asset but not required.

Key Skills & Attributes
• Excellent verbal and written communication skills.
• Strong interpersonal skills and professionalism.
• Ability to multitask in a fast-paced environment.
• Strong attention to detail and problem-solving abilities.
• Positive attitude, coachability, and commitment to growth.
• Ability to work independently and collaboratively.

Training & Development

Comprehensive onboarding, insurance fundamentals, product education, sales and relationship-building skills,
agency systems training, compliance education, personalized mentorship, performance coaching, and ongoing
development opportunities.

Career Opportunity

This program is designed to prepare high-potential candidates for a permanent Insurance Account
Representative role within the agency.

Individuals who successfully complete the training program and transition into a permanent position will have
access to:
• Competitive base salary
• Performance-based bonus opportunities
• Commission and incentive earnings
• Ongoing professional development and mentorship
• Career advancement opportunities

What We Offer

• Paid full-time training at an annualized salary of $45,000
• Comprehensive insurance and product education
• Structured onboarding and professional development
• One-on-one mentorship and ongoing coaching
• Hands-on client service and sales experience
• Supportive, collaborative team environment
• Opportunity to secure a permanent full-time Insurance Account Representative position upon successful
completion of the program

Eligibility Requirement

Candidates must be legally eligible to work in Canada.

Important Information

You will be hired to work at The Personal Insurance Company ("The Personal") for a period of up to 90 days to
allow you to complete training and licensing.

If training and licensing are successfully completed, you will be considered for employment with an independent
contractor for a Desjardins Agent.

We welcome applications from people with disabilities. Accommodations are available upon request for
applicants in all aspects of the recruitment process.

Start Your Career with Desjardins Insurance

If you are motivated to learn, passionate about helping people, and eager to build a long-term career in a
professional and supportive environment, we encourage you to apply.

Take the first step toward a rewarding career with Desjardins Insurance today.