Director of Field Sales, Central Region

About the role

Square is seeking a dynamic sales leader to scale its Field Sales organization in the Central Region. This role requires a proven track record of driving performance, building high-performing teams, and executing with speed and precision.

Responsibilities

• Lead a team of Sales Managers and Territory Account Executives to acquire and expand small and midsize businesses across key Central markets.
• Set and execute on a strategy to strengthen and expand the Central Field Sales organization.
• Drive to win by fostering a culture of performance, accountability, and competitiveness.
• Lead from the front by spending meaningful time in the field, co-selling, coaching, and demonstrating product fluency.
• Be a product expert, mastering Square's ecosystem and ensuring teams sell consultatively.
• Execute with speed and precision by managing pipeline health, conversion rates, and sales productivity.
• Think like a builder by 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.
• Represent Square locally by 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 in a similar role with a focus on driving sales growth and team development.
• Ability to travel up to 80% of the time.

Skills

• Strategic thinking and execution.
• Team leadership and development.
• Product knowledge and understanding.
• Market analysis and competitive intelligence.
• Customer relationship management.
• Financial acumen.

Benefits

Block offers a comprehensive benefits package including remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning. For more details, visit our Benefits page.

Pay

Pay varies depending on location and job-related skills, experience, qualifications, and market conditions. For more information, refer to the Pay section.

Schedule

Flexible schedule to accommodate remote work and travel requirements.