
Job Overview
Location
Chicago, IL, United States of America
Job Type
Full-time
Category
Account Executive
Date Posted
February 26, 2026
Full Job Description
đź“‹ Description
- • Join Block, Inc., a global technology company dedicated to increasing access to the global economy, and specifically, become a pivotal part of the Square team as a Territory Account Executive in Chicago.
- • Since our inception in 2009, we have been at the forefront of transforming commerce, starting with enabling anyone to accept payments and never miss a sale. As the commerce landscape evolved, so did Square, expanding into integrated, omnichannel software solutions to empower sellers with online sales, inventory management, buy now, pay later options, appointment booking, customer engagement tools, and staff management.
- • Our mission is to provide sellers of all sizes with the tools they need to grow, from startups to enterprise-level businesses. We embed financial services directly at the point of sale, offering business loans and cash flow management in one place. With the integration of Afterpay, we further enhance our ability to help sellers capture the next generation of shoppers, increase order values, and scale their operations.
- • This role is designed for a high-impact, execution-focused individual who thrives in dynamic, fast-paced environments and is driven to exceed expectations. You will be the face of Square in one of our most promising markets, taking full ownership of your territory.
- • Your primary responsibility will be to build and nurture relationships with local businesses, acting as their trusted advisor and Square’s competitive advantage. You will spend approximately 80% of your week in the field, actively engaging with potential and existing clients, conducting live product demonstrations, and closing deals.
- • This is a full-cycle, self-sourced sales role. You will be responsible for generating your own leads through a variety of methods, including door-to-door outreach, community engagement, networking events, and strategic partnerships.
- • Your day-to-day will involve identifying business needs, presenting Square’s comprehensive ecosystem of industry-leading software and hardware solutions, and guiding clients through the sales process to a successful close.
- • You will establish yourself as the go-to Square expert within the Chicago market. This involves building strong, trust-based relationships with local sellers by consistently being present, reliable, and delivering tangible value.
- • A key aspect of this role is to foster a disciplined referral strategy, transforming every new customer into a source of future opportunities and expanding Square’s reach within the community.
- • You will collaborate cross-functionally with internal teams to ensure a seamless onboarding experience for new sellers, accelerating their time-to-value and solidifying their success with Square.
- • Developing a repeatable, high-velocity pipeline is crucial. You will achieve this by mastering your verticals, which include key industries such as restaurants, retail, and services. Deep expertise in these sectors will enable you to accurately diagnose business challenges and effectively position the most relevant Square solutions.
- • The sales motion is consultative and competitive. You will need to remain proactive, strategic, and highly organized throughout the entire sales cycle, from initial contact to closing the deal.
- • Operational rigor is paramount. You will maintain meticulous records in Salesforce, diligently tracking all activities, managing your pipeline effectively, and providing accurate sales forecasts.
- • Continuous improvement is expected. You will be encouraged to measure your performance frequently, identify areas for growth, and implement strategies to enhance your effectiveness.
- • Ultimately, your success will be measured by your ability to consistently exceed sales quotas in a high-accountability environment where high standards are the norm. This is an opportunity to make a significant impact on local businesses and contribute directly to Square’s mission of economic empowerment.
- • You will be empowered to lead your market with disciplined, in-person execution, driving significant growth and establishing Square as the preferred commerce solution for businesses in Chicago.
- • This role offers the chance to develop deep expertise in key verticals, enabling you to speak the language of your clients and offer tailored solutions that address their specific pain points and growth objectives.
- • By building a robust referral engine and leveraging community engagement, you will create a sustainable and scalable sales model that fuels long-term success for both yourself and the businesses you serve.
- • You will be an integral part of building a best-in-class, high-impact field sales organization, contributing to a culture of high performance and continuous learning.
- • Your ability to operate strategically and decisively in a dynamic market will be key to your success and the success of the businesses you partner with.
- • This position is ideal for a motivated, results-oriented individual eager to join a team with high standards and a commitment to making a meaningful difference in the economic landscape.
- • You will be instrumental in helping local businesses thrive by providing them with the integrated tools and financial services they need to compete and grow in today's competitive market.
- • Embrace the challenge of building a territory from the ground up, establishing a strong presence, and driving substantial revenue growth for Square.
- • This role demands a proactive, entrepreneurial spirit, a passion for sales, and a deep understanding of how technology can empower businesses.
- • You will be a key player in Square's mission to democratize commerce and financial services, bringing essential tools to the businesses that form the backbone of our communities.
- • Your success will be directly tied to your ability to execute consistently, build strong relationships, and deliver exceptional value to your clients.
- • This is more than just a sales job; it's an opportunity to be a catalyst for business growth and economic empowerment in the vibrant Chicago market.
Skills & Technologies
Remote
$148k-223k
Degree Required
About Block, Inc.
Block, Inc. builds financial technology and commerce tools for businesses and consumers. Its ecosystem spans Square point-of-sale systems, Cash App peer-to-peer payments, Afterpay buy-now-pay-later services, and Bitcoin-focused initiatives including TBD and hardware wallets. Operating globally, the company offers integrated hardware, software, and banking solutions that enable sellers to accept payments, manage inventory, obtain loans, and sell online, while giving individuals access to digital banking, stock investing, and cryptocurrency services.
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