Ready to make an impact?

We’re looking for talented people ready to shape the future of insurance and make a real impact.

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Come work with us

Our aim is to create a workforce that is diverse, promotes positivity, and demonstrates the values of equality, fairness, and respect in everything we do. We are dedicated to an antidiscrimination approach and provide equal opportunity for employment regardless of gender, race, ethnicity, national origin, age, sexual orientation or identity, education, or disability. We respect and value diverse life experiences and cultures and ensure that all voices are valued and heard.

Southampton Financial Inc. welcomes and encourages applications from people with disabilities. Accommodations are available on request for candidates taking part in all aspects of the selection process.

For any requests, questions, or accommodation needs, please contact us at careers@shfi.ca

Our Brands

Whether you're drawn to a role within one of our brands or are interested in contributing to the broader vision of Southampton, we are always looking for passionate individuals who are ready to make an impact. Our employees are at the heart of everything we do, and we believe in providing an environment where talented people can grow, collaborate, and thrive.

Explore the opportunities available across all of our brands and discover how you can be part of our journey to redefine the insurance landscape.

Insurance Advisor, Sales (remote or hybrid) Full time

Southampton Group of Companies has recently acquired Onlia Insurance. We're not just merging companies, we are fusing expertise, innovation, and a relentless commitment to excellence. We are here to disrupt insurance in Canada and are building a team of heavy hitters to make that a reality. We work collaboratively in a fast-paced and agile environment. Every member of our team is empowered to take ownership of their role, and to assist in the build of a best-in-class experience for our customers.

We’re seeking a motivated Insurance Advisor - Sales to drive new business growth and deliver exceptional client service in a fast-paced brokerage environment. You’ll manage a high volume of inbound calls and online leads, close sales over the phone, and consistently meet or exceed monthly sales targets.

This role focuses on understanding client needs, recommending appropriate coverage with integrity, and ensuring compliance with underwriting guidelines. You’ll also identify cross-sell and upsell opportunities, collaborate closely with insurance underwriters, and stay current on insurer products and portals through ongoing training.

This is a full-time position, Monday to Friday during standard business hours. The role is open to candidates both in and outside of Ontario. At Onlia Insurance, you’ll have the opportunity to grow your sales career, make a direct impact on business results, and be supported by a team that values performance, professionalism, and continuous development.

Onlia Insurance logo featuring a stylized cloud with a speech bubble tail.

Insurance Advisor, Sales (remote) Full time

Our Mission:

Cheep Insurance isn’t your typical insurance brokerage. As Atlantic Canada’s first fully digital insurance broker, we’ve been shaking things up in the industry since 2016! Our mission is to make insurance simple, convenient, and accessible to everyone. We specialize in personal insurance solutions with an emphasis on specialty segments and are committed to ensuring that all individuals can secure the insurance they need. Cheep is the brokerage of choice for many Atlantic Canadians and joining the Southampton Group of Companies has opened the door to meeting the needs of Canadians in Ontario & Alberta as well. The journey of expanding our reach across Canada means we are also growing our fantastic team of professionals!

We’re seeking a motivated Insurance Advisor - Sales to drive new business growth and deliver exceptional client service in a fast-paced brokerage environment. You’ll manage a high volume of inbound calls and online leads, close sales over the phone, and consistently meet or exceed monthly sales targets.

This role focuses on understanding client needs, recommending appropriate coverage with integrity, and ensuring compliance with underwriting guidelines. You’ll also identify cross-sell and upsell opportunities, collaborate closely with insurance underwriters, and stay current on insurer products and portals through ongoing training.

This is a full-time position, Monday to Friday during standard business hours. The role is open to candidates both in and outside of Ontario. At Cheep Insurance, you’ll have the opportunity to grow your sales career, make a direct impact on business results, and be supported by a team that values performance, professionalism, and continuous development.

Key Accountabilities:

  • Meeting and/or exceeding monthly and annual sales goals while providing excellent customer service

  • Converting leads into sales using the company’s sales processes & tools (including Zoho, automated follow-ups, etc. )

  • Managing leads assigned in Zoho and the quotes folder in a timely manner. Ensuring all emails and voicemails receiving in allotted time slot are followed up with promptly. If this isn’t possible, please communicate with the Sales Manager so leads can be reassigned.

  • Helping Cheep Insurance achieve its goal of increasing polices per client by up-selling & cross-selling

  • Capturing current data for leads for marketing purposes

  • Maintaining relationships with underwriters and business development reps

  • Bringing any issues or potential areas of improvement to Management’s attention

  • Familiarization with the binding authority the Employer has with various insurance carriers it writes business for and the correct procedures for submitting business to each company which must be adhered to – including but not limited to The Facility Register, online portals, real time upload via the company BMS, etc. The Employee acknowledges that binding authority and underwriting rules may vary by province for each insurer, an agrees to maintain and understanding of and abide by the rules for each province

  • Keep informed of, familiar with, and up-to-date on changes in rating, policy eligibility and underwriting guidelines of various insurance carriers.

  • Maintain a solid understanding of the payment processes and options offered by each insurance company and financing partner the Employer represents (Direct Bill vs. IFS), and ensure that all policies and procedures for each are followed.

  • Support the company’s vision and values

  • Support and uphold the company’s policies regarding Compliance, Health & Safety and Corporate Culture by displaying the appropriate behaviors and leadership towards meeting the company’s objectives in these areas.

Qualifications and Competencies:

  • Active insurance license in one or more of the Atlantic provinces

  • Nice to have: RIBO, licensing in any of the Western provinces

  • Working toward CAIB/CIP designation if not already held

  • Understanding of the product offerings and processes of our insurer partners

  • Excellent written and verbal communication skills

  • Post-secondary education and / or equivalent on the job experience

  • Minimum of 3 years’ experience in insurance broker sales (home and Auto)

  • High level of integrity and excellent work ethic

  • Demonstrate effective sales skills through needs-based consultative selling

  • High energy results-oriented individual with a proven track record in sales

  • Ability to work in fast-paced and challenging environment

  • Ability to prioritize and manage conflicting demands independently

  • Ability to work individually as well as part of a team

  • Proficiency with computer applications including EPIC (Broker Management System), Zoho, Applied Rating Services (ARS) and Microsoft Office

Compensation & Perks:

  • Base Salary + Commission

  • Fully Remote

  • Generous Vacation & Wellness package

  • Extended Health Benefits

WORKING AT CHEEP INSURANCE

Our mission is to cultivate a workforce that is diverse and inclusive, with an unwavering commitment to creating an open, equitable, and respectful workplace for all. We are deeply dedicated to fostering an environment where every individual is genuinely respected, included, and empowered to contribute their unique perspectives and talents.

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.

Cheep Insurance logo