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Head of Sales

Billyard Insurance Groupabout 22 hours ago
Mississauga, Ontario, Canada
CA$90,000 - CA$130,000/year
Senior Level
Full-Time

Top Benefits

Base salary $90k–130k CAD
Performance-based upside tied to team production
High earning potential

About the role

Head of Sales (Build & Scale a High-Performance Brokerage Team)

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.

What You’ll Own Build and scale a team of producing brokers Design and implement a repeatable orientation + 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

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.

About Billyard Insurance Group

Insurance Agencies and Brokerages