Job Summary
Head of Sales
Billyard Insurance Group - Mississauga East
Full-time
In-Office | Mississauga, ON, Canada
The Opportunity
This is an opportunity for someone who wants to do more than manage a team, it’s for someone who wants to build one. You will play a direct role in shaping the future growth of the brokerage by recruiting strong talent, developing high-performing brokers, and creating the systems and culture that drive consistent production. This role offers real ownership, visibility, and impact within a fast-growing environment where results matter and strong leadership is rewarded. For the right person, this is a chance to build something meaningful, scale a team your way, and grow alongside a company that is actively expanding.
What You’ll Own
Build and scale a team of producing brokers
Own recruiting outcomes (not HR — actual results)
Design and implement a repeatable onboarding + training system
Drive daily sales activity (calls, appointments, conversions)
Track and improve key metrics:
Conversion rates
Time to first deal
Revenue per broker
Identify underperformance early and act quickly
Create a strong accountability culture
What Success Looks Like
More hires becoming productive within 30–60 days
Improved retention of new brokers
Consistent, predictable sales output
Who You Are
You’ve built or scaled a sales team (not just managed one)
Background in a commission-heavy sales environment
(insurance, mortgage, auto, call center, or similar)
You are metrics-driven and operate with clear KPIs
Comfortable holding people accountable
You’ve hired, trained, and fired people before
You coach in real time, not just theory
Compensation
Base: $90,000 – $130,000 CAD
Performance-based upside tied to team production
High earning potential for the right person
Why This Role
Real ownership over building the sales organization
Direct impact on growth
No corporate layers or bureaucracy
Opportunity to build something meaningful and scale it
We’re a growing brokerage entering our next phase of expansion.
We are not looking for a traditional “sales manager.”
We are looking for a builder, someone who can recruit, train, and scale a high-performing team of brokers in a commission-driven environment.
To Apply
Include answers to:
Describe a sales team you personally built or significantly improved (include metrics).
How would you take 10 new hires and get at least 5 producing within 30–60 days?
What metrics do you track daily to manage performance?
Applications without these answers will not be considered.
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