Director of Field Sales, Central Region

The Role

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

You will lead Sales Managers and Territory Account Executives focused on acquiring and expanding small and midsize businesses across key Central markets. You'll set strategy, drive execution, and foster a culture that's fast, focused, and fiercely competitive—all while serving as a product expert who deeply understands and champions the Square ecosystem.

This is an opportunity to take a growing field organization and build it into a scalable, high-performing regional powerhouse that delivers consistent, measurable impact. You Will

• Scale with purpose: Strengthen and expand the Central Field Sales organization by refining territory models, optimizing go-to-market plans, and instilling operational rigor.
• Drive to win: Build a culture grounded in performance, accountability, and competitiveness—where teams are motivated to exceed targets and celebrate excellence.
• Lead from the front: Spend meaningful time in the field—co-selling, coaching, and demonstrating product fluency through action.
• Be a product expert: Master Square's ecosystem end-to-end and ensure your teams sell consultatively—connecting product capabilities to seller outcomes.
• Execute with speed and precision: Drive predictable, data-backed growth by managing pipeline health, conversion rates, and sales productivity.
• Think like a builder: Continuously improve systems, tools, and playbooks to help the team sell smarter and scale faster.
• Collaborate to amplify impact: Partner with Marketing, Sales Ops, Partnerships, and Product to align regional execution with national strategy and feedback loops.
• Inspire and develop talent: Attract, retain, and grow high-performing sales professionals who are hungry to win and advance their careers.
• Represent Square locally: Serve as the face of Square's brand and mission across key Central markets—connecting with business leaders, partners, and communities.

About the role

There is a massive opportunity in front of us. We're building a significant, meaningful, and lasting business, and we are helping sellers worldwide do the same.

Responsibilities

You Will

• Scale with purpose: Strengthen and expand the Central Field Sales organization by refining territory models, optimizing go-to-market plans, and instilling operational rigor.
• Drive to win: Build a culture grounded in performance, accountability, and competitiveness—where teams are motivated to exceed targets and celebrate excellence.
• Lead from the front: Spend meaningful time in the field—co-selling, coaching, and demonstrating product fluency through action.
• Be a product expert: Master Square's ecosystem end-to-end and ensure your teams sell consultatively—connecting product capabilities to seller outcomes.
• Execute with speed and precision: Drive predictable, data-backed growth by managing pipeline health, conversion rates, and sales productivity.
• Think like a builder: Continuously improve systems, tools, and playbooks to help the team sell smarter and scale faster.
• Collaborate to amplify impact: Partner with Marketing, Sales Ops, Partnerships, and Product to align regional execution with national strategy and feedback loops.
• Inspire and develop talent: Attract, retain, and grow high-performing sales professionals who are hungry to win and advance their careers.
• Represent Square locally: Serve as the face of Square's brand and mission across key Central markets—connecting with business leaders, partners, and communities.

Requirements

Required:

• 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

Preferred:

• Block takes a market-based approach to pay, and pay may vary depending on your location.
• Zones A - D: 304,000 - 456,000
• Amounts listed above include target variable compensation.

Skills

Master Square's ecosystem end-to-end and ensure your teams sell consultatively—connecting product capabilities to seller outcomes.

Benefits

Block is an equal opportunity employer evaluating all employees and job applicants without regard to identity or any legally protected class. We will consider qualified applicants with arrest or conviction records for employment in accordance with state and local laws and “fair chance” ordinances. We believe in being fair, and are committed to an inclusive interview experience, including providing reasonable accommodations to disabled applicants throughout the recruitment process. We encourage applicants to share any needed accommodations with their recruiter, who will treat these requests as confidentially as possible.

Pay

Block, Inc. (NYSE: XYZ) builds technology to increase access to the global economy. Each of our brands unlocks different aspects of the economy for more people. Square makes commerce and financial services accessible to sellers. Cash App is the easy way to spend, send, and store money. Afterpay is transforming the way customers manage their spending over time. TIDAL is a music platform that empowers artists to thrive as entrepreneurs. Bitkey is a simple self-custody wallet built for bitcoin. Proto is a suite of bitcoin mining products and services. Together, we’re helping build a financial system that is open to everyone.

Schedule

Remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning are just some of our offerings.