Field Sales Director, Central Region

Square; Chicago (IL); On-site; USD 180,000 - 240,000; Full time

Job summary

Square is seeking a driven, entrepreneurial sales leader to scale our Field Sales organization across the Central Region. This high-impact role combines startup scrappiness with operational discipline, thriving on competition and turning promising teams into durable growth engines.

You will lead Sales Managers and Territory Account Executives focused on acquiring and expanding small and midsize businesses in Central markets.

Qualifications

• 10+ years of sales experience.
• 5+ years leading regional or field sales teams.
• Experience in high-growth SaaS/fintech/payments.
• Proven track record of exceeding revenue goals.

Responsibilities

• Scale the Central Field Sales organization with territory refinement and disciplined go-to-market plans.
• Drive performance and accountability, exceeding targets.
• Lead from the front with field coaching and hands-on product fluency.
• Be a product expert who connects Square capabilities to seller outcomes.
• Drive pipeline health, conversion, and productivity with data-driven rigor.

Skills

Sales leadership

Team building

SaaS experience

Fintech domain

Job description

Since we opened our doors in 2009, the world of commerce has evolved immensely, and so has Square. After enabling anyone to take payments and never miss a sale, we saw sellers stymied by disparate, outmoded products and tools that wouldn't work together.

So we expanded into software and started building integrated, omnichannel solutions – to help sellers sell online, manage inventory, offer buy now, pay later functionality, book appointments, engage loyal buyers, and hire and pay staff. Across it all, we've embedded financial services tools at the point of sale, so merchants can access a business loan and manage their cash flow in one place. Afterpay furthers our goal to provide omnichannel tools that unlock meaningful value and growth, enabling sellers to capture the next generation shopper, increase order sizes, and compete at a larger scale.

Today, we are a partner to sellers of all sizes – large, enterprise-scale businesses with complex operations, sellers just starting, as well as merchants who began selling with Square and have grown larger over time. As our sellers grow, so do our solutions. 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.

The Role

Since we opened our doors in 2009, the world of commerce has evolved immensely, and so has Square. After enabling anyone to take payments and never miss a sale, we saw sellers stymied by disparate, outmoded products and tools that wouldn't work together.

So we expanded into software and started building integrated, omnichannel solutions – to help sellers sell online, manage inventory, offer buy now, pay later functionality, book appointments, engage loyal buyers, and hire and pay staff. Across it all, we've embedded financial services tools at the point of sale, so merchants can access a business loan and manage their cash flow in one place. Afterpay furthers our goal to provide omnichannel tools that unlock meaningful value and growth, enabling sellers to capture the next generation shopper, increase order sizes, and compete at a larger scale.

Today, we are a partner to sellers of all sizes – large, enterprise-scale businesses with complex operations, sellers just starting, as well as merchants who began selling with Square and have grown larger over time. As our sellers grow, so do our solutions. 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.

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.

You Have

• 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