BIG Oakville is one of our original branches and a cornerstone of the Billyard Insurance Group story. With a team of seasoned professionals, many of whom have been with the branch for over a decade, this location has built a reputation for loyalty, depth of expertise, and consistent high performance. Joining BIG Oakville means stepping into a stable, tight-knit team that knows how to win and takes genuine pride in who they are. This branch is also a standout in commercial lines, making it a compelling home for brokers who want to grow their commercial expertise alongside a strong personal lines foundation.
As a Sales Broker at BIG Oakville, you will join a high-performing, experienced team backed by one of Canada's most recognized insurance brands. You will have the freedom to build your book of business your way, supported by industry-leading technology, strong insurer relationships, and an in-house service team that handles the day-to-day so you can stay focused on growth.
What You'll Do
- Generate new leads through digital outreach, referrals, networking, and community engagement.
- Conduct in-depth client needs assessments and recommend tailored insurance solutions across personal and commercial lines.
- Deliver competitive quotes using comparative rating tools and insurer portals.
- Negotiate with underwriters to secure the best balance of coverage and pricing for your clients.
- Finalize new business and accurately capture all documentation in the Broker Management System (BMS).
- Partner with our in-house Account Management and service team, with the opportunity to buy into a serviced book so you can focus on sales while your clients are in expert hands.
- Identify cross-sell and upsell opportunities to deepen client relationships and strengthen retention.
- Grow your commercial lines expertise alongside experienced colleagues who are leaders in that space.
- Maintain compliance with RIBO standards, insurer guidelines, and E&O protocols.
- Participate in ongoing training through BIG U and contribute to a team culture built on shared success.
What We're Looking For
- A client-focused professional with a strong track record in insurance sales.
- Someone who communicates clearly, builds trust quickly, and thrives in a self-directed environment.
- A relationship builder who treats clients as long-term partners, not transactions.
- Someone with genuine interest in growing their commercial lines capabilities.
- Comfortable with technology including Broker Management Systems, comparative rating tools, and digital sales workflows.
- Organized, compliant, and detail-oriented with accurate files and strong E&O discipline.
- Collaborative by nature but accountable to their own results.
Qualifications
- High school diploma or equivalent (post-secondary in business or finance an asset).
- Minimum 2 years of experience in insurance sales or a high-performance sales environment.
- Active RIBO license or willingness to convert your OTL.
- CAIB or CIP designation an asset.
What We Offer
Compensation and Structure
- Uncapped commissions on new business and renewals*
- 3-month paid base salary to support your ramp-up, designed for experienced brokers making a confident transition.
- Ownership interest in the book of business you build
- Three months of in-office training and onboarding in Oakville to set you up right then the option for a hybrid model.
Support and Tools
- Option to buy into a serviced book of business, providing a foundation for long-term income and growth.
- Proprietary AI-driven technology for underwriting, analytics, and lead management.
- Strong carrier relationships and broad market access across personal and commercial lines.
- Digital leads, sales workflows, and marketing support to fuel your pipeline.
Team and Culture
- Join one of BIG's original and most tenured branches, a loyal and high-performing team with deep roots.
- A commercial lines environment where you can genuinely grow your expertise.
- BIG U ongoing training and access to internal underwriting specialists.
- A people-first culture built on collaboration, integrity, and real support.
Compensation Disclosure
*The first three months of employment include a base salary for qualifying experienced candidates. Following this ramp-up period, this role transitions to a commission-based structure compensated exclusively through uncapped commissions on new and renewal business. Subject to applicable agreements and regulatory requirements, individuals may become eligible over time to retain an ongoing interest in the book of business they personally generate.
Diversity, Inclusion and Belonging
Billyard Insurance Group Oakville is committed to building a transparent environment where everyone feels heard, welcomed, and included. We are a proud equal-opportunity workplace committed to equal employment opportunity regardless of race, colour, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, or gender identity.
Accessibility
BIG Oakville is committed to an inclusive, barrier-free recruitment process. Should you require any accommodation, please contact us at [email protected] or 905.346.2190 ext. 10112 and we will work with you to meet your accessibility needs.
BIG does not use AI to screen or assess candidates. This posting is to fill a new open role within our organization.
Pay: $50,000.00-$100,000.00 per year
Application question(s):
- Will you be able to reliably commute or relocate to Oakville for the first 3 months of training?
- I understand that this role is paid through uncapped commissions with a base for 3 months training only.
Experience:
- Insurance: 2 years (preferred)
- Sales: 2 years (preferred)
Licence/Certification:
- RIBO or OTL License (required)
Work Location: Hybrid remote in Oakville, ON L6M 1L9
