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 merchants
Build pipeline through cold outreach and targeted campaigns
Develop tailored multi-product solutions across Square’s ecosystem
Conduct discovery, demos, negotiations, and complex deal closing




Maintain Salesforce pipeline discipline and forecasting accuracy
Requirements: Five-plus years of full-cycle B2B sales experience
Consistent quota achievement and net-current business creation
Experience closing complex, multi-threaded deals
Exceptional communication, presentation, and negotiation skills
Advanced Salesforce proficiency and a bachelor’s degree or equivalent
Use outbound prospecting, consultative selling, and Salesforce expertise to grow Square’s mid-market merchant base.

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