Enterprise Account Executive, Commerce Remote Chicago, IL, US
Afterpay
- SEE ALL JOBS; Enterprise Account Executive, Commerce Apply Remote Chicago, IL, US Req ID: R0005550 Posted Date: 09/15/26 Posted yesterday Apply Job DetailsApply 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