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Insurance Sales Agent Trainee Jobs in Calgary, AB

Management Trainee

Calgary, AB · On-site

CA$56K/yr

Whether you see yourself in sales, business development, customer service, retail management, or ... Life Insurance; Prescription coverage * Employee discounts on car rentals, car purchases and much ...

Whether you see yourself in sales, business development, customer service, retail management, or ... Life Insurance; Prescription coverage * Employee discounts on car rentals, car purchases and much ...

Whether you see yourself in sales, business development, customer service, retail management, or ... Life Insurance; Prescription coverage * Employee discounts on car rentals, car purchases and much ...

Management Trainee

Cochrane, AB · On-site

CA$56K/yr

Whether you see yourself in sales, business development, customer service, retail management, or ... Life Insurance; Prescription coverage * Employee discounts on car rentals, car purchases and much ...

... Sales Support team. Reporting to the manager administrative support. Our team stands out for its ... Flexible group insurance * Generous pension plan * Employee Share Ownership Plan * Employee and ...

Showing results 21-40

Insurance Sales Agent Trainee information

What is an insurance sales agent trainee?

Insurance Sales Agent Trainees are entry-level professionals who are learning the skills and knowledge required to sell insurance policies to clients. They typically work under the supervision of experienced agents or managers while undergoing training in sales techniques, company policies, and insurance products. The position helps trainees gain the necessary licenses and experience to become fully licensed insurance sales agents. Their main responsibilities include prospecting for clients, understanding their insurance needs, and learning to match those needs with suitable insurance products.

What are the key skills and qualifications needed to thrive as an insurance sales agent trainee?

To thrive as an Insurance Sales Agent Trainee, you need strong sales aptitude, basic knowledge of insurance products, and typically a high school diploma or equivalent, with many roles requiring completion of state insurance licensing. Familiarity with customer relationship management (CRM) software, quoting tools, and digital communication platforms is common, and passing the relevant state licensing exam is often mandatory. Excellent interpersonal communication, resilience, and active listening are standout soft skills that help build client trust and drive sales success. These abilities are crucial for effectively matching clients with appropriate policies and achieving sales targets in a competitive, client-focused industry.

What are some common challenges faced by insurance sales agent trainees during their initial training period?

New Insurance Sales Agent Trainees often face challenges such as quickly learning complex insurance products, adapting to various sales techniques, and building a client base from scratch. It's typical to balance studying for licensing exams with hands-on training and shadowing experienced agents. Trainees may also need to overcome initial rejection from potential clients, but with support from mentors and ongoing training, most find their confidence and skills grow steadily over the first few months.

What is the difference between Insurance Sales Agent Trainee vs Insurance Sales Agent?

AspectInsurance Sales Agent TraineeInsurance Sales Agent
CredentialsTypically requires a license, some states require pre-licensing coursesMust hold an active license and meet ongoing licensing requirements
Work EnvironmentTraining environment, often supervised, in offices or remotelyIndependent or team-based sales in offices, client homes, or remotely
Job RoleLearning sales techniques, product knowledge, and licensing proceduresSelling insurance policies, managing client relationships, and meeting sales targets

In summary, an Insurance Sales Agent Trainee is in the learning phase, focusing on gaining necessary licenses and skills, while an Insurance Sales Agent is actively selling policies and managing client accounts with an active license.

What are the most commonly searched types of Insurance Sales Agent jobs in Calgary, AB?

The most popular types of Insurance Sales Agent jobs in Calgary, AB are:

What cities near Calgary, AB are hiring for Insurance Sales Agent Trainee jobs?

Cities near Calgary, AB with the most Insurance Sales Agent Trainee job openings:

Infographic showing various Insurance Sales Agent Trainee job openings in Calgary, AB as of August 2026, with employment types broken down into 1% As Needed, 75% Full Time, 20% Part Time, and 4% Contract. Highlights an 89% Physical, 2% Hybrid, and 9% Remote job distribution.

Field Sales Agent - Calgary North **$500 Signing Bonus! Ask for Details**

OSL Direct Services

Calgary, AB

CA$18/hr

Full-time

Medical, Dental, Vision

Re-posted 15 days ago


Job description

Overview

Field Sales Agents | Calgary North and Surrounding Area

This position is eligible for a $500 Signing Bonus! Please ask for Details

OSL is a dynamic, people-driven company providing outsourced sales services. We celebrateunique and energetic people that work together to deliver incredible results; great people doing great things every day! We have a hunger to succeed and never miss an opportunity to recognize and celebrate each other's milestones. We support those around us, and we're always pushing each other to reach new heights. If you're interested in joining an award-winning team, and one of Canada's Top 50 Best Managed Companies for the past 8 years in a row, this is the place.Your success leads to our success, and your growth leads to our continued growth. 

We're looking for enthusiastic, friendly, and customer-focused Field Sales Agents, for one of our incredible clients, HelloFresh. In this D2D sales role, you'll be going door-to-door to meet potential clients face to face. You'll introduce them to our fantastic line of products and help them find easy, innovative ways to reach their health and wellness goals!

What's Offered:

  • Competitive hourly wage $18/hour plus uncapped commission
  • Annual reviews including potential for Wage Increases
  • Mileage expenses and Overtime Pay
  • Continuous incentives including daily and monthly bonuses 
  • Referral Bonuses - As an employee, you can refer friends or family to work with us! If they get hired and stay, you get paid!
  • Benefits including Medical, Dental, Vision, Accidental, Hospital, and Critical Illness Insurance
  • Training and development opportunities to grow your career
  • Strong support from Team Leads, Area Managers, and Directors - you will feel like you are part of a strong team!
  • Opportunity to work with one Canada's Best Managed Companies (8 years running!)

What does it take to succeed in this role?

  • Willingness to Learn: We provide the tools, and we'll train you to succeed!
  • Winning Attitude: You bring a positive mindset to work every day! For you, the customer's satisfaction is always #1
  • Charisma: A natural ability to connect with people and deliver our best-in-class customer experience as an OSL Field Sales Agent
  • Teamwork: Meet with the team weekly to strategize innovations, track goals, and report on sales and marketing results
  • Professionalism: Conduct yourself with optimism, empathy, and integrity as the face of our client
  • Determination: In sales, you might hear many No's before you get to a Yes. You not only understand this, but you welcome it!
  • Adaptability: We work outdoors in all weather conditions, it hasn't stopped us before and it's not going to stop us now!

 

What are we looking for in an ideal candidate?

  • Previous sales experience isn't a must, but it is an asset
  • Previous experience in a Direct Sales, Customer Service, and/or a Marketing role is considered an asset
  • You are 18+ years old and authorized to work in Canada on a permanent basis
  • You are an outgoing, people person; helping and being around people naturally gives you energy
  • You are an expert in time management, evaluating priorities, and accomplishing weekly goals
  • You are money-motivated and driven to win
  • You have a demonstrated ability to be a team player
  • You have reliable access to personal vehicle and a valid Class 5 (or higher) driver's license
  • You have a flexible full-time schedule that includes the ability to work during evenings and weekends as needed

With thousands of meal-kit options and billions of units sold, HelloFresh and Factor continue to be market leaders in the space and have proven that people are excited to make better, easier, faster meals that are not only healthier, but can even contribute less annual food-waste when compared to an every-day grocery run. This isn't your average retail or sales associate role, instead, we train you how to partner with clients and provide a consultative approach to sales. And just so you know, yes, we promote from within, so if you're successful in this role there will be opportunities to grow your career with us.

Sounds like a great fit? Apply today! We're excited to meet you!

At OSL, we celebrate difference. We've committed to fostering an inclusive and accessible workplace where everyone feels valued, supported, and reaches their full potential.

OSL does not discriminate against race, nationality, religion, age, marital status, physical or mental disability, sexual orientation, gender, or gender identity. We believe in diversity and encourage any qualified individual to apply.

Employment Type: OTHER