Block

Field Sales Director, Central Region

Chicago, IL, United States of America. Posted a month ago

The role

You will lead Sales Managers and Territory Account Executives to acquire and expand small and midsize businesses. You will set strategy, drive execution, and scale the Central Field Sales organization.

What you will do

  • Strengthen and expand the Central Field Sales organization
  • Build a culture grounded in performance, accountability, and competitiveness
  • Spend time in the field co-selling, coaching, and demonstrating product fluency
  • Master Square's ecosystem end-to-end
  • Manage pipeline health, conversion rates, and sales productivity
  • Improve systems, tools, and playbooks
  • Partner with Marketing, Sales Ops, Partnerships, and Product
  • Attract, retain, and grow high-performing sales professionals
  • Serve as the face of Square's brand across key Central markets

Required qualifications

  • 10+ years of sales experience
  • 5+ years leading regional or field sales teams in a high-growth SaaS, fintech, or payments environment
  • Proven success driving overperformance and exceeding regional revenue and productivity goals
  • Proven track record of building high-performance teams
  • Strong product acumen
  • Builder mindset
  • Deep operational expertise in forecasting, pipeline management, and KPI tracking
  • Excellent communication and executive presence

Benefits

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

About the company

Block, Inc. builds technology to increase access to the global economy. Its brands include Square, Cash App, Afterpay, TIDAL, Bitkey, and Proto.

Field Sales Director, Central Region at Block | JobZoey