Director of Field Sales, Central Region (Chicago)

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 wouldn't 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, we've 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. We're building a significant, meaningful, and lasting business, and we are helping sellers worldwide do the same.The RoleSquare 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.You WillScale 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.You Have10+ 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 candidate's 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 location's 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: 304,000 - 456,000Amounts listed above include target variable compensation.We're 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 we're doing to build a workplace that is fair and square? Check out ourI+D page.Application GuidelinesCandidates may submit up to 9 active applications within a 60-day period. Reapplications to the same role are accepted 90 days after a previous application has been reviewed.Use of AI in Our Hiring ProcessWe may use automated AI tools to evaluate job applications for efficiency and consistency. These tools comply with local regulations, including bias audits, and we handle all personal data in accordance with state and local privacy laws. Contact us here with hiring practice or data usage questions.Every benefit we offer is designed with one goal: empowering you to do the best work of your career while building the life you want. Remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning are just some of our offering. Check out our other benefits at Block.Block, Inc. (NYSE: XYZ) builds technology to increase access to the global economy. Each of our brands unlocks different aspects of the economy for more people. Square makes commerce and financial services accessible to sellers. Cash App is the easy way to spend, send, and store money. Afterpay is transforming the way customers manage their spending over time. TIDAL is a music platform that empowers artists to thrive as entrepreneurs. Bitkey is a simple self-custody wallet built for bitcoin. Proto is a suite of bitcoin mining products and services. Together, we’re helping build a financial system that is open to everyone.Privacy Policy