Drive Square’s mid-market growth through outbound selling, consultative discovery, and complex multi-product deals with merchants across diverse industries.
As a Senior Sales Account Executive on Square’s Mid-Market Team, you will build, shape, and close your own pipeline. You will manage sophisticated deals from prospecting through negotiation and final close. The work combines strategic execution, hunter instincts, and consultative selling.

Key Responsibilities

Own the full outbound sales cycle with mid-market merchantsBuild pipeline through cold outreach and targeted campaignsDevelop tailored multi-product solutions across Square’s ecosystemConduct discovery, demos, negotiations, and complex deal closingMaintain Salesforce pipeline discipline and forecasting accuracyRequirements:
Five-plus years of full-cycle B2B sales experienceConsistent quota achievement and net-recent business creationExperience closing complex, multi-threaded dealsExceptional communication, presentation, and negotiation skillsAdvanced Salesforce proficiency and a bachelor’s degree or equivalentUse outbound prospecting, consultative selling, and Salesforce expertise to grow Square’s mid-market merchant base.
#J-18808-Ljbffr

📌 Senior Mid-Market Sales Executive (Winnipeg)
🏢 Square
📍 Winnipeg