Director of Field Sales, Central Region

About the role

Square is seeking a driven, entrepreneurial sales leader to scale its Field Sales organization across the Central Region. This role requires a builder who combines startup scrappiness with operational discipline, someone who thrives on competition, inspires performance, and transforms promising teams into durable growth engines.

Responsibilities

• Lead Sales Managers and Territory Account Executives focused on acquiring and expanding small and midsize businesses across key Central markets.
• Set strategy, drive execution, and foster a culture that's fast, focused, and fiercely competitive.
• Spend meaningful time in the field—co-selling, coaching, and demonstrating product fluency through action.
• Be a product expert, mastering Square's ecosystem end-to-end and ensuring teams sell consultatively, connecting product capabilities to seller outcomes.
• Execute with speed and precision by driving predictable, data-backed growth through pipeline health, conversion rates, and sales productivity.
• Think like a builder, continuously improving systems, tools, and playbooks to help the team sell smarter and scale faster.
• Collaborate with Marketing, Sales Ops, Partnerships, and Product to align regional execution with national strategy and feedback loops.
• Inspire and develop talent by attracting, retaining, and growing high-performing sales professionals who are hungry to win and advance their careers.
• Represent Square locally by serving as the face of Square's brand and mission across key Central markets—connecting with business leaders, partners, and communities.

Requirements

• 10+ years of sales experience, including 5+ years leading regional or field sales teams in a high-growth SaaS, fintech, or payments environment.
• Proven success driving overperformance, with a track record of exceeding regional revenue and productivity goals.
• Proven track record of building high-performance teams and creating cultures grounded in coaching, accountability, and excellence.
• Strong product acumen, with the ability to position complex solutions across multiple product lines and use data to guide decisions.
• A builder mindset—move fast, stay resourceful, and operationalize what works at scale.
• Deep operational expertise in forecasting, pipeline management, and KPI tracking.
• Excellent communication and executive presence, with the ability to influence across all levels of the organization.

Qualifications

• Master's degree in Business Administration, Finance, Economics, or related field.
• Experience with CRM systems and sales analytics tools.
• Ability to travel up to 70% of the time.

Skills

• Exceptional sales and negotiation skills.
• Strong understanding of the payments industry and fintech trends.
• Ability to build and maintain strong relationships with clients and partners.
• Proficiency in Microsoft Office Suite.

Benefits

Block takes a market-based approach to pay, and pay may vary depending on your location. U.S. locations are categorized into one of four zones based on a cost of labor index for that geographic area. The successful candidate's starting pay will be determined based on job-related skills, experience, qualifications, work location, and market conditions. These ranges may be modified in the future. To find a location's zone designation, please refer to this resource. If a location of interest is not listed, please speak with a recruiter for additional information.

Pay

Zones A - D: $304,000 - $456,000

Schedule

Remote work available.

Contact Us

If you have any questions about the application process or hiring practices, please contact us here.