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SquareSquareIndianapolis, IN

Director of Field Sales, Central Region

Leads Field Sales Managers and Account Executives to acquire and expand small/midsize businesses in Central Region markets. Drives strategy, execution, team performance, and growth in high-growth SaaS/fintech environment; requires 10+ years sales experience including 5+ leading regional teams.

304k – 456k
On-site10+ YOEExecutive Leadership

About the role

Responsibilities

  • Scale the Central Field Sales organization by refining territory models, optimizing go-to-market plans, and instilling operational rigor.
  • Build a culture of performance, accountability, and competitiveness.
  • Spend time in the field co-selling, coaching, and demonstrating product fluency.
  • Master Square's ecosystem and ensure consultative selling.
  • Drive predictable growth through pipeline management, conversion rates, and sales productivity.
  • Improve systems, tools, and playbooks for smarter selling.
  • Collaborate with Marketing, Sales Ops, Partnerships, and Product.
  • Attract, retain, and develop high-performing sales professionals.
  • Represent Square locally in key Central markets.

Requirements

  • 10+ years of sales experience, including 5+ years leading regional or field sales teams in high-growth SaaS, fintech, or payments.
  • Proven success exceeding regional revenue and productivity goals.
  • Track record building high-performance teams with coaching and accountability.
  • Strong product acumen to position complex solutions and use data.
  • Builder mindset: fast, resourceful, scalable operations.
  • Deep expertise in forecasting, pipeline management, and KPI tracking.
  • Excellent communication and executive presence.

Compensation

  • Zones A - D: $304,000 - $456,000 (includes target variable compensation). Pay varies by location, skills, experience, and market conditions.

Skills

SaaS SalesFintech SalesPayments SalesPipeline ManagementForecastingKPI TrackingGo-to-Market StrategySales CoachingTerritory ManagementConsultative Selling

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