Enterprise Account Executive

About the role

Square is expanding its enterprise sales efforts to serve large, complex businesses. As an Enterprise Account Executive, you will be responsible for navigating multi-threaded sales cycles with executive stakeholders, focusing on technical integrations and cross-functional alignment.

Responsibilities

• Craft and Lead Deal Strategy: Develop sophisticated, insight-led sales narratives tailored to client business priorities. Identify the right entry points, map stakeholder influence, and build 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.

Requirements

• 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 collaborating 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 is 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.

Qualifications

• A BA/BS degree or equivalent professional experience.
• Willingness to travel ~40%.

Skills

• Exceptional communication and relationship-building skills.
• Ability to work independently and under pressure.
• Strong analytical and problem-solving skills.
• Knowledge of financial services and payment systems.

Benefits

Block offers competitive benefits, including remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning. Specific benefits may vary based on location and role.

Pay

Starting pay range varies based on location and experience, ranging from $144,979 to $395,400 annually.

Schedule

Full-time position.