Square is building a best-in-class, high-impact field sales organization, and we are looking for an exceptional Territory Account Executive — someone who consistently exceeds expectations, takes full ownership of their territory, and brings Square’s mission of economic empowerment directly to the businesses that need it most. This is a field-driven, execution-focused role designed for individuals who thrive in dynamic, demanding environments. You will spend most of your week out in the market — meeting businesses, conducting live demos, and closing deals with confidence. You will serve as Square’s presence and competitive advantage in one of our highest-opportunity markets — responsible for building pipeline from the ground up, elevating Square’s visibility in your community, establishing high-value partnerships, and helping local businesses grow through our ecosystem of industry-leading software and hardware. If you are motivated by impactful work, driven to outperform, and eager to join a high-performance team with high standards, this role is built for you. Lead your market with disciplined, in-person execution Spend ~80% of your week in the field — walking your territory, engaging local businesses, and driving 50–60 targeted business visits each week. Run a full-cycle, self-sourced sales motion: generate leads, identify needs, deliver compelling demos, and close deals across Square’s full product suite. Build strong, trust-based relationships with local sellers by being present, reliable, and value-driven. Implement a disciplined referral strategy to turn every new customer into future opportunities.



Build a high-velocity pipeline from the ground up Develop a repeatable top-of-funnel engine through door-to-door outreach, community engagement, events, networking, and targeted partnerships. Work with channel partners to generate a consistent, high-quality referral stream that grows over time. Build deep expertise in key verticals — including restaurants, retail, and services — to diagnose challenges and position the right Square solutions. Sell consultatively and competitively, staying proactive and strategic throughout the sales cycle. Maintain strong operational rigor in Salesforce: track activity, manage pipeline, and forecast accurately. Measure performance frequently and improve continuously. 3+ years of sales experience in a full cycle closing role with field sales experience ~ Experience exceeding sales targets, selling a diverse ecosystem of products, and closing complex deals ~ Since this is a field position, you must have reliable transportation and live in the market you are serving ~ Prior Salesforce experience or equivalent 2+ years of payment processing OR related technology (i.e. payroll, loyalty, time management) ~These tools comply with local regulations, including bias audits, and we handle all personal data in accordance with state and local privacy laws. Contact us here with hiring practice or data usage questions. Every benefit

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📌 Territory Account Executive, Halifax (Canada)
🏢 Block
📍 Canada