Director of Field Sales, Central Region

About the role

Square is seeking a driven, entrepreneurial leader to scale its Field Sales organization across the Central Region. This senior position combines startup scrappiness with operational discipline to build a high‑performing, data‑driven sales engine that fuels growth for small and midsize merchants.

Key responsibilities

• Lead Sales Managers and Territory Account Executives focused on acquiring and expanding SMB customers.
• Define and execute territory models, go‑to‑market plans, and operational rigor.
• Foster a performance‑focused culture that encourages accountability and competitive excellence.
• Spend significant time in the field co‑selling, coaching, and demonstrating product fluency.
• Act as a product expert for the Square ecosystem, guiding consultative selling.
• Manage pipeline health, conversion rates, and sales productivity with data‑backed insights.
• Continuously improve sales systems, tools, and playbooks.

Required profile

• Proven experience scaling field sales teams in a fast‑moving, technology‑driven environment.
• Entrepreneurial mindset with a track record of building durable growth engines.
• Strong leadership skills, able to inspire and motivate high‑performing teams.
• Comfortable operating in a competitive, results‑oriented culture.
• Ability to translate product capabilities into tangible seller outcomes.

Required skills