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Director of Field Sales, Central RegionBlock · Milwaukee, WI, United States of America
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Director of Field Sales, Central Region

🗓️ Posted 2026-07-20 Milwaukee, WI, United States of America Hybrid Sales
💰 Salary Not shared 📊 Market 15,000 CAD–25,000 CAD/mo

About the Company

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.

Responsibilities

  • ● Scale with purpose by strengthening and expanding the Central Field Sales organization by refining territory models, optimizing go-to-market plans, and instilling operational rigor.
  • ● Drive to win by building a culture grounded in 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 your teams sell consultatively-connecting product capabilities to seller outcomes.
  • ● Execute with speed and precision by driving predictable, data-backed growth by managing 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.