Territory Account Executive, Chicago

Responsibilities

• 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.

Requirements

• 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

Nice-to-Haves

• 2+ years of payment processing OR related technology (i.e. payroll, loyalty, time management)
• 1+ years of relevant audience experience (experience working in/selling to restaurants, retailers or services based businesses)