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 (Winnipeg)
🏢 Block
📍 Winnipeg