Enterprise Account Executive - Remote US

Square; Denver (CO); On-site; USD 245,000 - 368,000; Full time

Job summary

Square is seeking an experienced Enterprise Account Executive to lead high-value, multi-stakeholder deals from prospecting through closing. You will partner with Solutions Engineering on technical scoping and maintain alignment across Finance, Legal, Risk, and Product to drive complex sales in the payments and commerce ecosystem.

This role demands executive presence, exceptional communication, and the ability to operate independently in a fast-paced environment while traveling ~40% to engage

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 collaborates with Solutions Engineering teams.
• Proven ability to orchestrate multi-stakeholder deals — with exceptional communication, follow-through, and organizational discipline.
• Executive presence across conferences, boardrooms, and discovery calls with technical champions.
• Experience selling a complex ecosystem of SaaS or fintech products, ideally in payments, commerce, or adjacent verticals.
• Ability to operate independently in a fast-paced, ambiguous environment.
• Talent for translating complexity into clarity — simplifying technical integrations for CFOs or structuring ambiguous problems for internal stakeholders.
• BA/BS degree or equivalent professional experience.
• Willingness to travel ~40%

Responsibilities

• Craft and Lead Deal Strategy: Develop sophisticated, insight-led sales narratives tailored to client business priorities and build compelling ROI cases.
• Own the Full Sales Cycle: Manage pipeline end-to-end from prospecting to close with disciplined, rigorous qualification.
• Lead Technical, Complex Sales Cycles: Partner with Solutions Engineering to scope platform requirements and API integrations.
• Orchestrate Internal Alignment: Align Finance, Legal, Risk, Product, Solutions Engineering, and Account Management; surface blockers and maintain momentum.
• Represent Square at the Highest Level: Engage in executive meetings and industry events with polished, credible presence.
• Build Block's Enterprise Network: Develop relationships with senior leaders at leading brands and platform partners.
• Be a Multiplier for the Business: Influence product roadmaps and GTM strategy; leverage AI tools to sharpen research and workflow efficiency.

Skills

Enterprise sales

Executive presence

Payments domain

API integrations

SaaS / fintech

Travel willingness

Education

BA/BS degree or equivalent

Job description

Square is seeking an experienced Enterprise Account Executive to lead high-value, multi-stakeholder deals from prospecting through closing. You will partner with Solutions Engineering on technical scoping and maintain alignment across Finance, Legal, Risk, and Product to drive complex sales in the payments and commerce ecosystem.

This role demands executive presence, exceptional communication, and the ability to operate independently in a fast-paced environment while traveling ~40% to engage