Director Of Field Sales, Central Region

Square

Chicago, IL, United States
Base: $304,000 - $456,000 (includes target variabl...
On-site
10+ years of sales experience
5+ years leading regional sales teams
High-growth saas or fintech background
Square is seeking a driven sales leader to scale its Field Sales organization across the Central Region by refining territory models and optimizing go-to-market plans

Job Summary

  • Square is seeking a driven sales leader to scale its Field Sales organization across the Central Region by refining territory models and optimizing go-to-market plans.
  • The role requires a leader who can build a high-performance culture grounded in accountability while serving as a product expert to champion the Square ecosystem.
  • Candidates must have over 10 years of sales experience with a proven track record of exceeding regional revenue and productivity goals in high-growth environments.

Matching Summary

Square is seeking a driven sales leader to scale its Field Sales organization across the Central Region by refining territory models and optimizing go-to-market plans.

Salary

Base: $304,000 - $456,000 (includes target variable compensation); Bonus/Equity: Included in total range; Benefits: Remote work, medical insurance, flexible time off, retirement savings plans

Skills & Requirements

Must-have

  • 10+ years of sales experience
  • 5+ years leading regional sales teams
  • High-growth SaaS or fintech background
  • Proven track record exceeding revenue goals
  • Strong product acumen in payments ecosystem

Nice-to-have

  • Builder mindset with operational discipline
  • Experience in competitive sales cultures
  • Ability to co-sell and demonstrate products
  • Strategic partnership with marketing teams
  • Commitment to inclusive workplace values

Key Requirements

  • 10+ years of sales experience
  • 5+ years leading regional or field sales teams
  • Experience in SaaS, fintech, or payments environment
  • Deep operational expertise in forecasting and pipeline management

Work Rights

Not specified

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