Central Field Sales Leader: Build High-Impact SaaS Growth

Square; Chicago (IL); On-site; USD 180,000 - 240,000; Full time

Job summary

Square is seeking a driven, entrepreneurial sales leader to scale our Field Sales organization across the Central Region. This high-impact role combines startup scrappiness with operational discipline, thriving on competition and turning promising teams into durable growth engines.

You will lead Sales Managers and Territory Account Executives focused on acquiring and expanding small and midsize businesses in Central markets.

Qualifications

• 10+ years of sales experience.
• 5+ years leading regional or field sales teams.
• Experience in high-growth SaaS/fintech/payments.
• Proven track record of exceeding revenue goals.

Responsibilities

• Scale the Central Field Sales organization with territory refinement and disciplined go-to-market plans.
• Drive performance and accountability, exceeding targets.
• Lead from the front with field coaching and hands-on product fluency.
• Be a product expert who connects Square capabilities to seller outcomes.
• Drive pipeline health, conversion, and productivity with data-driven rigor.

Skills

Sales leadership

Team building

SaaS experience

Fintech domain

Job description

Square is seeking a driven, entrepreneurial sales leader to scale our Field Sales organization across the Central Region. This high-impact role combines startup scrappiness with operational discipline, thriving on competition and turning promising teams into durable growth engines.

You will lead Sales Managers and Territory Account Executives focused on acquiring and expanding small and midsize businesses in Central markets.