Lead outbound sales strategy and data-driven coaching as Square’s Senior Sales Manager, developing approximately 10 experienced Account Executives.

This senior leadership role manages a fully outbound team with self-sourced pipeline. You will coach Senior Account Executives with five-plus years of full-cycle closing experience. The work centers on talent development, forecasting, pipeline quality, and predictable growth.

Key Responsibilities:

- Hire exceptional Account Executives and raise talent standards
- Develop future leaders through structured growth plans
- Inspect pipeline health and diagnose performance gaps
- Establish forecasting, pipeline management, and business review rhythms
- Partner with Sales Leadership, Marketing, Enablement,



Operations, and Product

Requirements:

- Seven-plus years of sales management experience
- Three years of documented individual sales success exceeding target
- Experience leading high-performing sales teams
- Experience coaching outbound ICP targeting and multichannel strategies
- Deep expertise in pipeline management, forecasting, and data analysis

Apply sales leadership, outbound strategy, and business intelligence to strengthen Square’s Account Executive organization and commercial execution.

📌 Senior Outbound Sales Manager (Toronto)
🏢 Block
📍 Toronto