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

• Scale the Central Field Sales organization by refining territory models, optimizing go-to-market strategies, and instilling operational rigor.
• Drive to win by fostering a culture of performance, accountability, and competitiveness, where teams are motivated to exceed targets and celebrate excellence.
• 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 – 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

• Master’s degree in Business Administration, Finance, Economics, or related field.
• Experience in a similar role within a high-growth company.
• Ability to travel up to 70%.

Skills

• Exceptional leadership and interpersonal skills.
• Strategic thinking and the ability to execute on a plan.
• Strong negotiation and closing skills.
• Ability to build and maintain relationships with key stakeholders.
• Experience with CRM tools and sales analytics.

Benefits

Block offers a comprehensive benefits package that includes:

• Remote work options
• Medical insurance
• Flexible time off
• Retailer savings plans
• Modern family planning

Pay

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.

Schedule

Full-time position.