Field Sales Director, Central Region

Chicago, IL · US - IL - Chicago Metro - Remote · 5+ years experience · Remote · Posted Oct 9, 2026

At a glance

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 to transform 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.

Scale with purpose: Strengthen and expand the Central Field Sales organization by refining territory models, optimizing go-to-market plans, and instilling operational rigor.
Drive to win: Build a culture grounded in performance, accountability, and competitiveness where teams are motivated to exceed targets and celebrate excellence.
Lead from the front: Spend meaningful time in the field co-selling, coaching, and demonstrating product fluency through action.
Be a product expert: Master Square's ecosystem end-to-end and ensure your teams sell consultatively connecting product capabilities to seller outcomes.
Execute with speed and precision: Drive predictable, data-backed growth by managing pipeline health, conversion rates, and sales productivity.
Think like a builder: Continuously improve systems, tools, and playbooks to help the team sell smarter and scale faster.
Collaborate to amplify impact: Partner with Marketing, Sales Ops, Partnerships, and Product to align regional execution with national strategy and feedback loops.
Inspire and develop talent: Attract, retain, and grow high-performing sales professionals who are hungry to win and advance their careers.
Represent Square locally: Serve as the face of Square's brand and mission across key Central markets connecting with business leaders, partners, and communities.

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 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.