[Hiring] Enterprise Account Executive @Block

Role Description

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. 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.

Qualifications

• 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 — fluent in conversations involving API integrations, custom development, and platform configuration, and 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%.

Benefits

• Remote work.
• Medical insurance.
• Flexible time off.
• Retirement savings plans.
• Modern family planning.