Insurance Sales Representative jobs in Rama, ON

Our Mission:

Cheep Insurance isn’t your typical insurance brokerage. As Atlantic Canada’s first and only fully digital insurance broker, we’ve proudly been working from home since 2016—long before it became the norm. Since our launch, we’ve been shaking things up in the industry, and following our recent partnership with the Southampton Group of Companies, we’re ready to grow again!

We’re looking for a licensed Insurance Advisor with top-notch customer service skills to support our expanding book of business. This is a remote position requiring availability Monday to Friday during standard business hours. Applicants must have a reliable home workspace and be able to maintain consistent availability during their assigned shift.

At Cheep, you’ll be part of a small, energetic team that thrives on innovation, results, and a fun, tech-forward culture. If you're passionate about delivering exceptional service, embracing technology, and making a difference—while having a little fun along the way—this could be the perfect role for you.

Key Accountabilities:

1. Provide excellent customer service via phone or email.

2. Support retention goals by shopping policies and saving clients during cancellation inquiries.

3. Increase Cheep Insurance's online presence and positive Google reviews.

4. Ensure all necessary software is functioning for the duration of shifts and report issues.

5. Regularly review and update client files for accuracy.

6. Respond promptly to emails and voicemails, notifying the service manager if delays occur.

7. Check and action all email folders daily, including personal and shared ones.

8. Prioritize and address personal and team activities daily.

9. Help increase policies per client by cross-selling and upselling.

10. Attend monthly 1:1 coaching sessions and engage in team discussions.

Qualifications and Competencies:

• Post-secondary education and/or equivalent on the job experience
• A minimum of 2 years experience in personal lines insurance sales
• Active insurance license in at least one of the provinces we do business in (NS, NB, NL, PEI, & ON), with a willingness to get licensed across all others (PREFERENCE given to those who hold RIBO licensing)
• Willing to work toward CAIB or other additional licensing if needed
• In- depth understanding of our insurer partners’ product offerings and processes
• Excellent verbal and written communication skills
• Proficiency with computer applications including EPIC (Broker Management System), Applied Rating Services (ARS) and Microsoft Office
• Ability to work in a high customer engagement environment
• Ability to work individually as well as part of a team
• Ability to work in fast-paced and challenging environments
• Ability to manage and prioritize incoming requests by urgency and complexity, ensuring critical client needs to be addressed first
• Excellent email and phone etiquette
• High level of integrity and excellent work ethics
• Results orientated with a strong customer service focus
• Experience working with third-party premium finance companies (Imperial PFS preferred), including payment arrangements and cancellations for non-payment
• Strong understanding of high-risk and non-standard auto markets, including experience with Facility Association business and substandard underwriting guidelines
• Proven ability to manage complex billing scenarios and client communication related to financed policies and payment defaults
• Familiarity with carrier requirements and workflows for high-risk policies, including endorsements, cancellations, and reinstatements

WORKING AT CHEEP INSURANCE

Our mission is to simplify the insurance experience and help clients find the best price out there – quickly & easily. We invest in top technologies, continuously improve our workflows, and innovate to be the best we can every day. And unlike a lot of companies, we prioritize both the client and employee experiences to make sure everyone is happy.

We encourage submissions from candidates who represent the various dimensions of diversity. We are committed to providing barrier-free and accessible employment practices.

Cheep Insurance is an equal-opportunity employer and provides accommodations upon request to ensure all candidates feel comfortable and supported throughout the selection process.

Pay: $31,500.00-$41,500.00 per year

Benefits:

• Dental care
• Employee assistance program
• Extended health care
• Paid time off
• Vision care
• Work from home

Experience:

• Personal Lines Insurance Sales: 2 years (required)

Licence/Certification:

• RIBO License (preferred)
• Insurance License in the Atlantic Provinces (preferred)

Work Location: Remote