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Square is seeking a Manager of Field Sales to lead a world-class, high-accountability field sales organization in Toronto. This is a hands-on leadership role combining coaching, selling expertise, and team building.
In this role, you will develop Territory Account Executives through active, in-market coaching—from prospecting and discovery through competitive positioning and closing. You'll model world-class selling by joining prospect and customer meetings, demonstrating product fluency and value articulation. You'll spend significant time in the field with your team, strengthening local relationships and fueling community-driven pipeline creation.
You will manage pipeline and KPIs with rigor, diagnosing gaps, identifying risks, and guiding AEs to create and progress high-quality opportunities. You'll run disciplined weekly pipeline, forecast, and deal reviews that drive action, accountability, and predictable outcomes across multiple markets. Using data-backed insights, you'll coach AE effectiveness, elevate sales execution, and ensure consistent momentum across complex sales cycles.
You'll create a high-performance, high-accountability culture defined by trust, clear expectations, ownership, and open communication. You'll hire, onboard, and develop AEs to ramp quickly, deepen product expertise, and consistently exceed quota. You'll become a product and competitive expert, ensuring your team can confidently articulate Square's value and differentiation.
You'll build scalable, repeatable field sales motions that increase funnel quality, improve outbound productivity, and accelerate growth in assigned cities. You'll continuously refine strategy, playbooks, and operating rhythms to deepen Square's presence and win market share across key local ecosystems.
You'll champion the customer voice and collaborate cross-functionally to strengthen product-market fit and unlock new revenue pathways. You'll engage deeply with community networks, partners, and local events to amplify brand awareness and fuel top-of-funnel opportunity creation.
Square provides integrated, omnichannel commerce solutions—payments, software, inventory management, buy-now-pay-later, appointments, loyalty, payroll, and embedded financial services—serving sellers of all sizes globally.
