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Enterprise Account Executive, Commerce

Block (Square) · Chicago, IL, United States of America

$264k - $395k
On-site
Mid
20229 S&M - Sales - Commerce Enterprise and Mid

Posted September 15, 2026

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Job Description

It all started with an idea at Block in 2013. Initially built to take the pain out of peer-to-peer payments, Cash App has gone from a simple product with a single purpose to a dynamic ecosystem, developing unique financial products, including Afterpay/Clearpay, to provide a better way to send, spend, invest, borrow and save to our 50+ million monthly active customers. We want to redefine the world’s relationship with money to make it more relatable, instantly available, and universally accessible.

Today, Cash App has thousands of employees working globally across office and remote locations, with a culture geared toward innovation, collaboration and impact. We’ve been a distributed team since day one, and many of our roles can be done remotely from the countries where Cash App operates. No matter the location, we tailor our experience to ensure our employees are creative, productive, and happy.

The Role

The North American Enterprise team drives growth across our commerce and payments portfolio, including Afterpay and Cash App Pay. We partner with leading global brands to help them reach the next generation of consumers, create more flexible commerce experiences, and deliver measurable business results.
We are looking for an experienced enterprise seller to build and expand Block’s relationships with some of the world’s largest brands. You will identify new revenue opportunities, develop relationships with senior executives, and lead complex, often first-of-their-kind partnerships from initial strategy through negotiation, launch, and growth.

This role sits at the intersection of commerce, payments, technology, and consumer behavior. You will work closely with decision-makers across payments, marketing, digital commerce, finance, and technology while bringing together internal partners across Product, Engineering, Finance, Legal, Risk, Marketing, and Operations.
You will thrive in this role if you combine strong commercial instincts with strategic thinking, disciplined execution, and the ability to navigate ambiguity. Success requires persistence through long, multifaceted sales cycles, sound judgment, and the ability to create alignment across complex organizations.

You Will

  • Own the full enterprise sales cycle, from account strategy and opportunity creation through negotiation, contracting, launch, and expansion.
  • Build trusted relationships with senior executives at leading global brands and position Block as a strategic partner in commerce and payments.
  • Develop compelling, insight-led sales narratives that connect Cash App and Afterpay’s capabilities to each prospective partner’s priorities, customers, and growth strategy.
  • Lead complex and often first-of-their-kind deals using clear milestones, success measures, stakeholder alignment, and disciplined deal management.
  • Create thoughtful commercial strategies and negotiate pragmatic, mutually beneficial agreements informed by data, financial analysis, and business principles.
  • Coordinate cross-functional deal teams across Product, Engineering, Marketing, Finance, Legal, Risk, and Operations.
  • Translate merchant needs and market insights into actionable feedback that helps shape Block’s product and go-to-market strategy.
  • Build Block’s enterprise network by developing relationships across target accounts and representing Cash App and Afterpay at industry events and executive forums.
  • Maintain a strong understanding of the payments and commerce landscape, including emerging technologies, consumer trends, and competitive dynamics.
  • Consistently deliver against ambitious revenue goals while building a durable pipeline of strategic opportunities.

You Have

  • 8+ years of experience in enterprise sales, business development, partnerships, go-to-market strategy, or a related commercial role, ideally within technology, payments, financial services, or another high-growth environment.
  • Experience owning enterprise opportunities from initial prospecting and account planning through negotiation, contracting, launch, and expansion.
  • A demonstrated record of meeting or exceeding individual revenue or sales targets.
  • Experience closing enterprise agreements with extended sales cycles, multiple decision-makers, and cross-functional dependencies.
  • Experience developing account strategies and creating new revenue opportunities within large or global organizations.
  • Experience presenting commercial recommendations, proposals, and business cases to senior executives, including C-suite decision-makers.
  • Experience negotiating pricing, financial terms, commercial contracts, or other complex deal structures in partnership with Finance and Legal teams.
  • Experience using customer, market, revenue, and financial data to develop business cases and inform deal strategy.
  • Experience partnering with Product and Engineering teams during technical discovery, solution development, product scoping, or integration planning.
  • Experience coordinating cross-functional teams across functions such as Product, Engineering, Finance, Legal, Risk, Marketing, and Operations.
  • Experience managing sales forecasts, pipeline activity, and deal progress against defined milestones and performance targets.
  • Experience translating technical and commercial concepts for both technical and nontechnical audiences.
  • Familiarity with payments, financial technology, digital commerce, or consumer technology.
  • Willingness to travel as needed.

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.

Zone A: $263,600.00 - $395,400.00

Zone B: $245,120.00 - $367,680.00

Zone C: $232,000.00 - $348,000.00

Zone D: $224,080.00 - $336,120.00

Amounts 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 our I+D page.

While there is no specific deadline to apply for this role, U.S. roles are typically open for an average of 55 days before being filled by a successful candidate. Please refer to the date listed at the top of this job page for when this role was first posted.

Application Guidelines

Candidates 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 Process

We 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.

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