Director of Field Sales, Central Region

Since we opened our doors in 2009 the world of commerce has evolved immensely and so has Square. After enabling anyone to take payments and never miss a sale we saw sellers stymied by disparate outmoded products and tools that wouldnt work together.

So we expanded into software and started building integrated omnichannel solutions to help sellers sell online manage inventory offer buy now pay later functionality book appointments engage loyal buyers and hire and pay staff. Across it all weve embedded financial services tools at the point of sale so merchants can access a business loan and manage their cash flow in one place. Afterpay furthers our goal to provide omnichannel tools that unlock meaningful value and growth enabling sellers to capture the next generation shopper increase order sizes and compete at a larger scale.

Today we are a partner to sellers of all sizes large enterprise-scale businesses with complex operations sellers just starting as well as merchants who began selling with Square and have grown larger over time. As our sellers grow so do our solutions. There is a massive opportunity in front of us. Were building a significant meaningful and lasting business and we are helping sellers worldwide do the same.

The Role

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 disciplinesomeone 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. Youll set strategy drive execution and foster a culture thats fast focused and fiercely competitiveall 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.

You Will

• 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 competitivenesswhere teams are motivated to exceed targets and celebrate excellence.
• Lead from the front: Spend meaningful time in the fieldco-selling coaching and demonstrating product fluency through action.
• Be a product expert: Master Squares ecosystem end-to-end and ensure your teams sell consultativelyconnecting 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 Squares brand and mission across key Central marketsconnecting with business leaders partners and communities.

You Have

• 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.

Block takes a market-based approach to pay and pay may vary depending on your location. U.S. locations are categorized into one of four zones based on a cost of labor index for that geographic area. The successful candidates starting pay will be determined based on job-related skills experience qualifications work location and market conditions. These ranges may be modified in the future. To find a locations zone designation please refer to this resource. If a location of interest is not listed please speak with a recruiter for additional information.

Zones A - D: 304000 - 456000

Amounts listed above include target variable compensation.

Were working to build a more inclusive economy where our customers have equal access to opportunity and we strive to live by these same values in building our workplace. Block is an equal opportunity employer evaluating all employees and job applicants without regard to identity or any legally protected class. We will consider qualified applicants with arrest or conviction records for employment in accordance with state and local laws and fair chance ordinances. We believe in being fair and are committed to an inclusive interview experience including providing reasonable accommodations to disabled applicants throughout the recruitment process. We encourage applicants to share any needed accommodations with their recruiter who will treat these requests as confidentially as possible. Want to learn more about what were doing to build a workplace that is fair and square Check out our ID page.

Required Experience:

Director