Director of Field Sales, Central Region

Block•Chicago, IL

22h•$304,000 - $456,000

About The Position

Square is looking for a driven, entrepreneurial sales leader to scale our Field Sales organization across the Central Region. This is a high-impact role for a builder who combines startup scrappiness with operational discipline—someone who thrives on competition, inspires performance, and transforms promising teams into durable growth engines. You will lead Sales Managers and Territory Account Executives focused on acquiring and expanding small and midsize businesses across key Central markets. You'll set strategy, drive execution, and foster a culture that's fast, focused, and fiercely competitive—all while serving as a product expert who deeply understands and champions the Square ecosystem. This is an opportunity to take a growing field organization and build it into a scalable, high-performing regional powerhouse that delivers consistent, measurable impact.

Requirements

10+ years of sales experience
5+ years leading regional or field sales teams in a high-growth SaaS, fintech, or payments environment.
Proven success driving overperformance, with a track record of exceeding regional revenue and productivity goals.
Proven track record of building high-performance teams and creating cultures grounded in coaching, accountability, and excellence.
Strong product acumen, with the ability to position complex solutions across multiple product lines and use data to guide decisions.
A builder mindset —you move fast, stay resourceful, and operationalize what works at scale.
Deep operational expertise in forecasting, pipeline management, and KPI tracking.
Excellent communication and executive presence, with the ability to influence across all levels of the organization.

Responsibilities

Scale the Central Field Sales organization by refining territory models, optimizing go-to-market plans, and instilling operational rigor.
Build a culture grounded in performance, accountability, and competitiveness.
Spend meaningful time in the field—co-selling, coaching, and demonstrating product fluency through action.
Master Square's ecosystem end-to-end and ensure teams sell consultatively—connecting product capabilities to seller outcomes.
Drive predictable, data-backed growth by managing pipeline health, conversion rates, and sales productivity.
Continuously improve systems, tools, and playbooks to help the team sell smarter and scale faster.
Partner with Marketing, Sales Ops, Partnerships, and Product to align regional execution with national strategy and feedback loops.
Attract, retain, and grow high-performing sales professionals.
Serve as the face of Square's brand and mission across key Central markets—connecting with business leaders, partners, and communities.