[Remote] Enterprise Account Executive

Note: The job is a remote job and is open to candidates in USA. Square is a technology company that aims to increase access to the global economy through various financial services and commerce solutions. As an Enterprise Account Executive, you will manage high-value sales cycles, craft deal strategies, and collaborate with cross-functional teams to close complex deals. This role requires strong technical sales skills and the ability to engage with executive stakeholders.

Responsibilities

• 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

Skills

• 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%

Benefits

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

Company Overview

Company H1B Sponsorship