Enterprise Account Executive

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 Role

As an Enterprise Account Executive you will lead Square’s expansion into the country’s most strategic sellers.

This is a high-impact role for a proven enterprise seller who can identify the right opportunities, build strong executive relationships, and drive complex deals from first engagement through launch.

You will own accounts end-to-end—setting account strategy, generating pipeline, and closing high-value deals across multi-stakeholder buying groups with urgency. You’ll partner closely with Solutions Engineering, Product, Partnerships, Legal, and Finance to bring the full Square ecosystem to market.

We’re looking for someone who combines strong commercial judgment with disciplined execution, and who raises the bar on how enterprise deals are run.

You Will

• Own a targeted set of enterprise accounts
  Set clear priorities and be accountable for pipeline quality, deal progression, and closed revenue across your account set.
• Define and execute a clear account strategy
  Focus on the highest-impact opportunities and consistently convert pipeline into high-value wins.
• Lead complex, multi-stakeholder deals end-to-end
  Navigate executive, technical, and commercial stakeholders to drive alignment, accelerate decisions, and close deals at pace.
• Develop strong, insight-led account POVs
  Translate Square’s platform into differentiated value that advances deals and improves win rates.
• Run a disciplined, detail-oriented sales process
  Maintain momentum across long cycles, qualify rigorously, and increase conversion at each stage of the funnel.
• Partner cross-functionally to win
  Work across Solutions Engineering, Product, Partnerships, Legal, and Finance to remove blockers and close complex deals effectively.
• Represent Square with credibility at senior levels
  Build trusted relationships with executives that unlock access, influence decisions, and drive long-term partnerships.

You Have

• 8+ years of enterprise or strategic sales experience, with a consistent track record of exceeding targets and closing complex, high-value deals with full ownership
• Proven ability to build, qualify, and convert pipeline within a focused account set, with strong judgment on where to invest time and why
• Deep experience leading multi-threaded enterprise deals, navigating executive, technical, and procurement stakeholders with clarity and control
• Strong commercial acumen, with the ability to structure and negotiate deals thoughtfully across pricing, scope, and long-term value
• Executive presence and credibility—you communicate with precision, challenge constructively, and earn trust with senior decision-makers
• Experience selling a complex platform, SaaS, fintech, or payments solution into large or operationally sophisticated organisations
• A high standard for execution: you are disciplined, prepared, and follow through consistently, especially in long and ambiguous sales cycles
• A strong sense of ownership—you take responsibility for outcomes, not just activity, and operate effectively without heavy structure
• The ability to simplify complexity and drive clarity, both externally with customers and internally across teams

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 a proud equal opportunity employer. We work hard to evaluate all employees and job applicants consistently, without regard to identity or other legally protected class. 

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.

Block is a globally distributed company and this role will require working with other employees in multiple time zones. You may be required to perform work outside of normal business as part of this role