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 proven track record of building high-performance teams and creating cultures grounded in coaching, accountability, and excellence.

Responsibilities

• Scale the Central Field Sales organization by refining territory models, optimizing go-to-market plans, and instilling operational rigor.
• 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 through action.
• Be a product expert by 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 by continuously improving systems, tools, and playbooks to help the team sell smarter and scale faster.
• Collaborate to amplify impact by partnering 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.
• Strong product acumen, with the ability to position complex solutions across multiple product lines and use data to guide decisions.
• A builder mindset – you 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

• Proven ability to build and lead high-performing teams.
• Experience in scaling sales organizations and driving revenue growth.
• Strong understanding of the payment industry and fintech trends.
• Ability to communicate effectively with both technical and non-technical stakeholders.
• Passion for building a diverse and inclusive workplace culture.

Skills

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

Benefits

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

Pay

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

Schedule

Details on the schedule are not specified in the job posting.