Territory Account Executive - Calgary, Alberta 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 field driven, execution focused role is 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. Responsibilities Lead your market with disciplined, in-person execution: spend ~80% of your week in the field, 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. Establish yourself as the go-to Square expert in your city: build strong, trust-based relationships with local sellers, partner cross-functionally, implement a disciplined referral strategy. 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. Master your verticals and sell with precision: build deep expertise in key verticals—restaurants, retail, and services—to diagnose challenges and position the right Square solutions; sell consultatively and competitively. Achieve exceptional results in a high-accountability environment: maintain strong operational rigor in Salesforce, measure performance frequently, exceed quota. Qualifications 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. Ability to drive deals independently in a fast-paced, dynamic environment. Business development experience (e.g., hunting and cold calling). Reliable transportation and living in the market you are serving. Collaborative, team-player mentality. Prior Salesforce experience or equivalent. Preferred: 2+ years of payment processing or related technology (e.g., payroll, loyalty, time management). Preferred: 1+ year of experience working in/selling to restaurants, retailers, or services-based businesses. Compensation Block takes a market-based approach to pay, and pay may vary depending on your location. The starting pay will be determined based on skills, experience, qualifications, work location, and market conditions. Zone A: $159,900 - $239,900. Zone B: $159,900 - $239,900. Benefits Remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning are just some of our offerings. #J-18808-Ljbffr