Field Sales Director, Central Region

US - IL - Chicago Metro - RemoteFull-time$318k–$477k2026-10-09 → 2026-11-11

Core

Lead Field Sales organization to acquire and expand small and midsize businesses across Central markets using Square's omnichannel and financial services ecosystem.

Role type

Senior Field Sales Director (Regional)

Builds

Regional sales teams and revenue growth for SMBs

Domain

Fintech / Payments / SMB Commerce

Required skills

Regional sales leadership, SaaS/fintech sales experience, team building, product acumen, forecasting, pipeline management, executive presence

Preferred skills

Startup scrappiness, operational discipline, consultative selling

Technologies

Square ecosystem, CRM tools, data analytics platforms

Responsibilities

Scale field sales organization, drive revenue targets, coach sales managers and account executives, manage pipeline health, partner with product and marketing, represent brand in local markets

Seniority

Senior, hands-on IC

About Block

Block is one company built from many blocks, all united by the same purpose of economic empowerment. The blocks that form our foundational teams — People, Finance, Counsel, Hardware, Information Security, Platform Infrastructure Engineering, and more — provide support and guidance at the corporate level. They work across business groups and around the globe, spanning time zones and disciplines to develop inclusive People policies, forecast finances, give legal counsel, safeguard systems, nurture new initiatives, and more. Every challenge creates possibilities, and we need different perspective