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Field Sales Director, Central Region
$318K–$477K
Chicago, IL, United States of America +1 · Remote · Director · Full-time · Posted Oct 9, 2026
- Location
- Chicago, IL, United States of America
US - IL - Chicago Metro - Remote - Experience
- 10+ years of sales experience, including 5+ years leading regional or field sales teams.
About the job
Leads and scales Square’s Central Region field sales organization, driving seller acquisition and growth through team development, sales execution, and regional strategy.
What you'll do
- Refine territory models and go-to-market plans while managing pipeline health, conversion, and sales productivity.
- Coach and develop Sales Managers and Territory Account Executives, including field co-selling and product guidance.
- Partner with Marketing, Sales Ops, Partnerships, and Product to improve regional execution and represent Square in Central markets.
What they ask for
- 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 exceeding regional revenue and productivity goals and building high-performance teams.
- Strong product acumen and ability to position complex solutions across multiple product lines using data.
- Deep operational expertise in forecasting, pipeline management, and KPI tracking.
Pay
318,000 - 477,000 (total pay; includes target variable compensation)
Model-written summary · the original posting is authoritative