OTL Licensed Insurance Agent; Ontario

OTL Licensed Insurance Agent (Ontario)

Final date to receive applications: 18 September 2026

Department: Sales + Service

Employment Type: Permanent - Full Time

Location: Ontario, Canada

Compensation: $60,000 - $67,000 / year

Your Role

Your success in this role comes from your passion for helping people and your knowledgeable approach. You have strong social skills and genuinely believe it’s fun interacting with new people. You’re good at making real connections with potential clients because you have great listening skills. Once you know what a client needs, you take pride in being able to personalize a policy to those needs and, hopefully, to pass on some savings.

Over 90% of your day is spent on the phone, handling inbound calls and making outbound calls. You never pressure clients into buying a policy, but you’re also not scared to ask for the sale. Dealing with different calls and clients, you tailor your interaction to the situation  if challenges arise during a call, you take ownership and find graceful ways to deal with them.

One of the things you enjoy most about Square One is the supportive team environment. You’re never set up for failure; instead, you get all the coaching and training that you need to succeed.

Working in Square One’s call centre, you are the first and main point of contact for both potential and existing clients. As such, you have many important responsibilities, including:

• Handling a high volume of inbound calls from clients in a prompt and professional manner.
• Making outbound calls to clients who have received targeted marketing materials.
• Assessing client needs, providing quotes, and ultimately selling policies.
• Promoting Square One and encouraging clients to do the same.
• Responding to online chat and email inquiries from clients.
• Handling payment-related matters.
• Helping clients make changes to their policies.
• Taking claims reports from clients.
• Maintaining your training and industry knowledge.

As a member of the Square One team, you have a desire to direct your own work to achieve the responsibilities of your role. You do this by becoming an expert at what you do, and by working with a team that has a broader purpose than just making profit. Those who you work with would describe you as someone who:

• Enjoys working with others and has a passion for helping clients.
• Delivers excellent client service and possesses strong telephone skills.
• Communicates effectively when speaking with, or writing to, others.
• Uses active listening and questioning skills to understand needs and issues.
• Takes a consultative approach to selling.
• Handles objections and deals with rejection well.
• Works well under pressure, both independently and as part of a team.
• Pays close attention to detail.
• Uses sound judgement in making decisions and taking calculated risks.
• Adapts well to, and often initiates, change.
• Enjoys personal development and growth through learning.
• Provides and receives constructive feedback.

Your experience and education, combined with product and sales training we provide, helps ensure your success at Square One. For this role, you have:

• At least 2 years of experience selling property and/or auto insurance, preferably in a call centre environment.
• An active Other Than Life (OTL) General Insurance License in Ontario.
• At least 1 year of tenure with a recent employer.
• A high school diploma and, preferably, some post-secondary education.

You appreciate the fact that Square One tailors your compensation and benefits in the same way it tailors policies for its clients. Your very competitive compensation and benefits plan includes:

• Salary range: $60,000 - $67,000 annual.
• The ability to work from home.
• Flexible medical, dental, vision and extended health care coverage.
• Short and long-term disability coverage.
• Participation in the corporate profit‑sharing plan.