Director of Field Sales, Central Region

About the role

Square is seeking a seasoned 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

• 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 grounded in 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.
• 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

• Proven leadership in a high-growth environment.
• Experience in a similar role or related field.
• Ability to motivate and inspire teams to achieve results.
• Strong understanding of the Square ecosystem and its products.
• Experience in scaling sales teams and processes.

Skills

• Strategic thinking and execution.
• Effective communication and relationship-building skills.
• Ability to adapt to changing market conditions and customer needs.
• Strong analytical and problem-solving skills.
• Leadership and mentorship abilities.

Benefits

Block offers a comprehensive benefits package designed to empower you to do your best work and build the life you want. This includes remote work options, medical insurance, flexible time off, retirement savings plans, and modern family planning benefits. 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 provided pay range and contact a recruiter for details.

Schedule

Details on the schedule will be provided upon hire.