# Director of Field Sales, Central Region
**Company:** [Square](https://hotfix.jobs/companies/square)
**Location:** Chicago, IL
**Salary:** $304K-$456K
**Experience:** 10+ years
**Skills:** SaaS Sales, Fintech Sales, Payments Sales, Pipeline Management, Forecasting, KPI Tracking, Go-to-Market Strategy, Sales Coaching, Territory Management, Consultative Selling
**Posted:** 2026-05-07
> Leads Field Sales Managers and Account Executives to acquire and expand small/midsize businesses in Central Region markets. Drives strategy, execution, team performance, and growth in high-growth SaaS/fintech environment; requires 10+ years sales experience including 5+ leading regional teams.
## Job Description
## Responsibilities

- Scale the Central Field Sales organization by refining territory models, optimizing go-to-market plans, and instilling operational rigor.
- Build a culture of performance, accountability, and competitiveness.
- Spend time in the field co-selling, coaching, and demonstrating product fluency.
- Master Square's ecosystem and ensure consultative selling.
- Drive predictable growth through pipeline management, conversion rates, and sales productivity.
- Improve systems, tools, and playbooks for smarter selling.
- Collaborate with Marketing, Sales Ops, Partnerships, and Product.
- Attract, retain, and develop high-performing sales professionals.
- Represent Square locally in key Central markets.

## Requirements

- 10+ years of sales experience, including 5+ years leading regional or field sales teams in high-growth SaaS, fintech, or payments.
- Proven success exceeding regional revenue and productivity goals.
- Track record building high-performance teams with coaching and accountability.
- Strong product acumen to position complex solutions and use data.
- Builder mindset: fast, resourceful, scalable operations.
- Deep expertise in forecasting, pipeline management, and KPI tracking.
- Excellent communication and executive presence.

## Compensation

- Zones A - D: $304,000 - $456,000 (includes target variable compensation). Pay varies by location, skills, experience, and market conditions.
**Apply:** https://hotfix.jobs/jobs/director-of-field-sales-central-region-at-square-df22b0f9-d865-43fa-aefc-28e27033496b
**Canonical:** https://hotfix.jobs/jobs/director-of-field-sales-central-region-at-square-df22b0f9-d865-43fa-aefc-28e27033496b