Territory Account Executive, Pittsburgh

Pittsburgh, PA · US - PA - Remote · USD 128,960-193,440 · 1+ years experience · Remote · Posted Sep 25, 2026

At a glance

Square is building a best-in-class, high-impact field sales organization, and we are looking for an exceptional Territory Account Executive.
This is a field-driven, execution-focused role designed for individuals who thrive in dynamic, demanding environments.
You will serve as Square’s presence and competitive advantage in one of our highest-opportunity markets.

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.
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.
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.
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.
Maintain strong operational rigor in Salesforce: track activity, manage pipeline, and forecast accurately.

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 live in the market you are serving
A collaborative and team player mentality
Prior Salesforce experience or equivalent