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Insurance Sales Associate Jobs in Kitchener, ON (NOW HIRING)

Account Associate I

Kitchener, ON ยท Hybrid

CA$52/hr

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

Controls sales assignments by allocating necessary time to retention and acquisition goals ... Insurance and Short Term Disability. As well as a Stock Purchase Plan, Company match on RRSP, and ...

New

Account Associate I

Kitchener, ON ยท Hybrid

CA$52/hr

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

Controls sales assignments by allocating necessary time to retention and acquisition goals ... Insurance and Short Term Disability. As well as a Stock Purchase Plan, Company match on RRSP, and ...

New

Account Associate I

Kitchener, ON ยท Hybrid

CA$52/hr

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

Controls sales assignments by allocating necessary time to retention and acquisition goals ... Insurance and Short Term Disability. As well as a Stock Purchase Plan, Company match on RRSP, and ...

New

Group Underwriting Consultant

Kitchener, ON ยท Hybrid

CA$90/hr

  • Retirement

  • PTO

About The Wawanesa Mutual Insurance Company Founded in 1896, The Wawanesa Mutual Insurance Company ... They partner closely with the Sales team and are responsible for analyzing the and determining the ...

Sales Lead Canada

Waterloo, ON

  • Medical

  • Dental

  • Vision

  • PTO

JOB SUMMARY To assist store management with basic store operations, developing associates, and ... Benefits offered may include medical, vision, and dental insurance, a vacation package, and ...

Sales Lead Canada

Waterloo, ON ยท On-site

  • Medical

  • Dental

  • Vision

  • PTO

JOB SUMMARY To assist store management with basic store operations, developing associates, and ... Benefits offered may include medical, vision, and dental insurance, a vacation package, and ...

Sales Lead Canada

Waterloo, ON ยท On-site

  • Medical

  • Dental

  • Vision

  • PTO

JOB SUMMARY To assist store management with basic store operations, developing associates, and ... Benefits offered may include medical, vision, and dental insurance, a vacation package, and ...

Sales Lead Canada

Kitchener, ON

  • Medical

  • Dental

  • Vision

  • PTO

JOB SUMMARY To assist store management with basic store operations, developing associates, and ... Benefits offered may include medical, vision, and dental insurance, a vacation package, and ...

Associate Accountant

Burlington, ON ยท On-site

CA$55K - CA$70K/yr

  • Medical

  • Dental

  • Vision

  • Life

  • PTO

... Sales & Marketing, and senior leadership to keep every dollar on track from groundbreaking to ... Full coverage for dental, prescriptions, vision, paramedical, life insurance and more for you and ...

Wealth Associate (On-Site)

Hamilton, ON ยท On-site

  • Medical

  • Retirement

Carry out routine operations related to financial transactions (e.g., purchases and sales of ... Two years of relevant experience in the banking ("back office"), insurance, and/or financial ...

Showing results 41-60

Insurance Sales Associate information

See Kitchener, ON salary details

$14.9K

$40.9K

$76.5K

How much do insurance sales associate jobs pay per year?

As of Aug 12, 2026, the average yearly pay for insurance sales associate in Kitchener, ON is $40,912.00, according to ZipRecruiter salary data. Most workers in this role earn between $28,922.00 and $48,981.00 per year, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive as an insurance sales associate, and why are they important?

To thrive as an Insurance Sales Associate, you need strong sales skills, product knowledge, and often a state insurance license. Familiarity with CRM software, quoting tools, and underwriting systems is typically required. Outstanding communication, active listening, and relationship-building abilities help you connect with clients and close sales. These skills are essential for meeting sales targets, ensuring customer satisfaction, and complying with industry regulations.

Is it hard to make money in insurance sales?

Insurance sales associates can earn varying income levels based on commissions, sales skills, and client base. Success often depends on building relationships, product knowledge, and persistence, with income potentially increasing as experience and sales volume grow.

What are some common challenges faced by insurance sales associates, and how can they be overcome?

Insurance Sales Associates often encounter challenges such as building a steady client base, handling rejections, and keeping up with changing insurance products. Success in this role requires persistence, strong interpersonal skills, and continuous learning. Many associates find it helpful to develop effective networking strategies, leverage CRM tools, and participate in ongoing training offered by their agency or company. Collaboration with experienced team members and seeking mentorship can also provide valuable support and insight.

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

AspectInsurance Sales AssociateInsurance Agent
CredentialsTypically requires a license, sometimes a certification depending on stateRequires a state license to sell insurance products
Work EnvironmentOften works in insurance offices, call centers, or retail locationsWorks independently or with agencies, meeting clients in person or remotely
Employer & Industry UsageEmployed by insurance companies or agencies, focusing on sales supportRepresents insurance companies or agencies, selling policies directly to clients
Common Search & ComparisonOften compared for entry-level roles or sales positions in insuranceCompared for licensed professionals selling insurance policies

In summary, Insurance Sales Associates typically support sales efforts and may require licensing, but their role is more focused on assisting and customer service. Insurance Agents are licensed professionals who directly sell insurance policies and represent insurance companies or agencies. Both roles are essential in the insurance industry but differ mainly in responsibilities and licensing requirements.

What does an insurance sales associate do?

An Insurance Sales Associate helps clients understand and purchase insurance policies that best fit their needs, such as auto, home, health, or life insurance. They explain policy options, answer questions, and process applications. Additionally, they may follow up with clients to review coverage and assist with claims or policy updates. Their role combines customer service, product knowledge, and sales skills to build lasting client relationships.
What cities near Kitchener, ON are hiring for Insurance Sales Associate jobs? Cities near Kitchener, ON with the most Insurance Sales Associate job openings:
Infographic showing various Insurance Sales Associate job openings in Kitchener, ON as of August 2026, with employment types broken down into 1% As Needed, 63% Full Time, 32% Part Time, and 4% Contract. Highlights an 88% Physical, 1% Hybrid, and 11% Remote job distribution, with an average salary of $40,912 per year, or $19.7 per hour.

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

OSL Direct Services

Hamilton, ON โ€ข On-site

CA$18/hr

Full-time

Medical, Dental, Vision

Re-posted 9 days ago


Job description

Overview

Field Sales Agents | Hamilton, ON and Surrounding Area

*This position is eligible for a $500 Signing Bonus! Please ask for full 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.ย 

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, weekly and monthly bonuses
  • Referral Bonusesย - 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!

ย 

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 driver's license (This is a travelling role, you will be driving to different neighborhoods within the assigned market daily)
  • You have a flexible full-time schedule that includes the ability to work during evenings and weekends as required

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.

Job Posting Status:

  • This position is for an existing vacancy within our GTA West Team

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.

As part of our recruitment process, we utilize artificial intelligence (AI)-based tools to assist with certain stages, including initial resume screening and skills-matching assessments. These tools are designed to help our hiring team identify candidates whose experience and qualifications align closely with the requirements of the role. Please note that all final hiring decisions are made by our recruitment and/or hiring manager team. If you have questions or concerns about this process, please feel free to contact us at info@oslrs.com.

Employment Type: OTHER