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 standardsDevelop future leaders through structured growth plansInspect pipeline health and diagnose performance gapsEstablish forecasting, pipeline management, and business review rhythmsPartner with Sales Leadership, Marketing, Enablement, Operations, and ProductRequirements:

Seven-plus years of sales management experienceThree years of documented individual sales success exceeding targetExperience leading high-performing sales teamsExperience coaching outbound ICP targeting and multichannel strategiesDeep expertise in pipeline management, forecasting, and data analysisApply sales leadership, outbound strategy, and business intelligence to strengthen Square’s Account Executive organization and commercial execution.

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