Territory Account Executive, New Haven

Block•New Haven, CT

4h•Onsite

About The Position

Since its inception in 2009, Square has evolved significantly, expanding beyond payment processing to offer integrated, omnichannel solutions. These solutions help sellers manage online sales, inventory, buy now/pay later functionality, appointments, customer engagement, and staff hiring/payment. Square also embeds financial services tools for business loans and cash flow management. With the addition of Afterpay, Square aims to provide tools that unlock value and growth for sellers, enabling them to reach the next generation of shoppers and compete at a larger scale. Square partners with businesses of all sizes, from startups to large enterprises, and is committed to building a significant, meaningful, and lasting business globally. Square is building a best-in-class, high-impact field sales organization and is seeking an exceptional Territory Account Executive. This role is for someone who consistently exceeds expectations, takes full ownership of their territory, and directly brings Square's mission of economic empowerment to businesses. It is a field-driven, execution-focused position for individuals who thrive in dynamic, demanding environments, spending most of the week in the market meeting businesses, conducting live demos, and closing deals. The successful candidate will serve as Square's presence and competitive advantage in a high-opportunity market, responsible for building pipeline, elevating Square's visibility, establishing high-value partnerships, and helping local businesses grow through Square's ecosystem of software and hardware. This role is ideal for those motivated by impactful work, driven to outperform, and eager to join a high-performance team with high standards.

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)

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.