Lead approximately 10 Senior Account Executives at Square through data-driven coaching, outbound strategy, and high-performance team development.

As a Senior Sales Manager, you will develop experienced Account Executives with five-plus years of full-cycle closing experience. You will improve pipeline quality, forecasting, business decisions, and execution through structured coaching. The team sources pipeline through executive networks, partnerships, trade shows, and intent data.

Key Responsibilities:

- Hire exceptional Account Executives and raise the talent bar
- Develop future leaders through structured growth plans
- Inspect pipeline, forecast performance, and diagnose business trends
- Establish operating rhythms for forecasting and business reviews




- Partner with Sales Leadership, Marketing, Enablement, Operations, and Product

Requirements:

- Seven-plus years of sales management experience
- Three years exceeding targets as an individual contributor
- Experience leading high-performing outbound sales teams
- Expertise in pipeline management, forecasting, and business intelligence
- Experience hiring talent and developing Account Executives

Shape predictable growth at Square through outbound sales leadership, pipeline discipline, data, and Account Executive development.

📌 Senior Mid-Market Sales Manager (Toronto)
🏢 Square
📍 Toronto