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'll be the tip of the spear for Square's most strategic, high-value deals. You'll navigate multi-threaded sales cycles with executive stakeholders involving technical integrations and cross-functional alignment. This is a role for a seasoned enterprise seller who owns the full deal lifecycle — from cold outreach to signed contract — and thrives in the complexity that comes with it.

You'll join a high-performing enterprise sales team that is deeply supported and strategically prioritized. Square is making significant investments to bring Square upmarket at scale and enable enterprise sales success. This is a team that operates with rigor, moves with urgency, and takes pride in signing the largest deals for the company.

You Will

• Craft and Lead Deal Strategy: Develop sophisticated, insight-led sales narratives tailored to client business priorities. You will identify the right entry points, mapping stakeholder influence, and building compelling business cases that create clear ROI.
• Own the Full Sales Cycle: Manage your pipeline end-to-end with precision — from prospecting and discovery through negotiation and close — qualifying rigorously and driving momentum at every stage without losing sight of the details
• Lead Technical, Complex Sales Cycles: Partner closely with Solutions Engineering to scope platform requirements and API integrations. Translate deeply technical concepts into language that resonates with executive decision-makers and know when to bring in the right expert at the right moment
• Orchestrate Internal Alignment: Quarterback cross-functional stakeholders across Finance, Legal, Risk, Product, Solutions Engineering, and Account Management — proactively surfacing blockers, resolving ambiguity, and ensuring everyone is aligned and moving in the same direction
• Represent Square at the Highest Level: Represent Square in C-suite meetings, on stage at industry conferences, or in working sessions with a prospect's technical team — with executive presence that is polished, credible, and authentic
• Build Block's Enterprise Network: Represent Square at industry events, trade shows, and networking functions; develop lasting relationships with senior leaders at leading brands and platform partners
• Be a Multiplier for the Business: Channel the voice of the customer internally to influence product roadmaps and go-to-market strategy; apply AI tools to sharpen your research, automate workflows, and increase your overall output

You Have

• 8+ years of enterprise sales experience, with a track record of closing complex, high-value deals with end-to-end ownership
• Deep experience in technical sales cycles — you're fluent in conversations involving API integrations, custom development, and platform configuration, and you collaborate naturally with Solutions Engineering teams
• A proven ability to orchestrate multi-stakeholder deals — internally and externally — with exceptional communication, follow-through, and organizational discipline
• Executive presence that's equally at home on a conference stage, in a C-suite boardroom, or on a discovery call with a technical champion
• Experience selling a complex ecosystem of SaaS or fintech products, ideally in payments, commerce, or adjacent verticals
• The ability to operate independently in a fast-paced, ambiguous environment — you don't wait to be told what to do next
• A talent for translating complexity into clarity — whether that's simplifying a technical integration for a CFO or structuring an ambiguous problem for an internal stakeholder
• A BA/BS degree or equivalent professional experience
• Willingness to travel ~40%

Why This Role

Square is growing our upmarket sales motion. We've built the infrastructure, the product depth, and the brand credibility to compete at the highest level — and we're accelerating. This role is for someone who wants to be at the center of that momentum: closing deals that matter, building relationships that last, and helping shape what enterprise sales looks like at one of the most consequential companies in commerce