Territory Account Executive, Sheffield

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. The pace is fast, the expectations are high, and your ability to operate strategically and decisively will determine your success.

You Will

• 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.
• Establish yourself as the go‑to Square expert in your city.
• Build strong, trust‑based relationships with local sellers by being present, reliable, and value‑driven.
• Partner cross‑functionally to ensure a seamless onboarding experience and fast time‑to‑value for new sellers.
• 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.
• Master your verticals and sell with precision.
• 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.
• Achieve exceptional results in a high‑accountability environment.
• Maintain strong operational rigor in Salesforce: track activity, manage pipeline, and forecast accurately.
• Measure performance frequently and improve continuously.
• Consistently exceed quota within a culture where high standards are the norm.

You Have

• 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).
• Since this is a field position, you must have reliable transportation and live in the market you are serving.
• A collaborative and team‑player mentality.
• Prior Salesforce experience or equivalent.
• Even better: 2+ years of payment processing OR related technology (e.g. payroll, loyalty, time management).
• 1+ years of relevant audience experience (experience working in/selling to restaurants, retailers or services‑based businesses).

We’re working to build a more inclusive economy where our customers have equal access to opportunity, and we strive to live by these same values in building our workplace. Block is an equal‑opportunity employer evaluating all employees and job applicants without regard to identity or any legally protected class. We will consider qualified applicants with arrest or conviction records for employment in accordance with state and local laws and “fair chance” ordinances. Every benefit we offer is designed with one goal: to empower you to do the best work of your career while building the life you want. Remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning are just some of our offerings.