Territory Account Executive, Chicago

Since we opened our doors in 2009, the world of commerce has evolved immensely, and so has Square. After enabling anyone to take payments and never miss a sale, we saw sellers stymied by disparate, outmoded products and tools that wouldn’t work together. So we expanded into software and started building integrated, omnichannel solutions – to help sellers sell online, manage inventory, offer buy now, pay later functionality, book appointments, engage loyal buyers, and hire and pay staff.

Across it all, we’ve embedded financial services tools at the point of sale, so merchants can access a business loan and manage their cash flow in one place. Afterpay furthers our goal to provide omnichannel tools that unlock meaningful value and growth, enabling sellers to capture the next generation shopper, increase order sizes, and compete at a larger scale. Today, we are a partner to sellers of all sizes – large, enterprise-scale businesses with complex operations, sellers just starting, as well as merchants who began selling with Square and have grown larger over time.

As our sellers grow, so do our solutions. There is a massive opportunity in front of us. We’re building a significant, meaningful, and lasting business, and we are helping sellers worldwide do the same.

The Role 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 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.

The territory for this role can be located in Riverside, Corona, or San Bernardino. 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.