Square is looking for a proven enterprise seller to lead its expansion into the country's most strategic accounts. As the US market leader in point-of-sale systems and a cohesive commerce ecosystem helping sellers start, run, and grow their businesses, Square offers an extraordinary platform to sell and a genuinely high-impact environment for enterprise sales professionals who take full ownership of their results. This is a high-ownership, high-visibility role for someone who can identify the right opportunities, build trusted executive relationships, and drive complex deals from first engagement through to launch.

In this role, you will own a targeted set of enterprise accounts end to end, setting account strategy, generating pipeline, and closing high-value deals across multi-stakeholder buying groups with clarity and urgency. You will define and execute a clear account strategy focused on the highest-impact opportunities and consistently convert pipeline into high-value wins. Leading complex, multi-stakeholder deals from first contact through close, you will navigate executive, technical, commercial, and procurement stakeholders to drive alignment and accelerate decisions. You will develop strong, insight-led account points of view that translate Square's platform into differentiated value, improving win rates and advancing deals. Maintaining momentum across long sales cycles, qualifying rigorously, and increasing conversion at each stage of the funnel will define how you work. You will partner cross-functionally with Solutions Engineering, Product, Partnerships, Legal, and Finance to remove blockers and close complex deals effectively, and represent Square with credibility and precision at senior levels, building the trusted executive relationships that unlock access and drive long-term partnerships.

The ideal candidate brings eight or more years of enterprise or strategic sales experience, with a consistent track record of exceeding targets and closing complex, high-value deals with full ownership. You have proven ability to build, qualify, and convert pipeline within a focused account set, with strong judgement on where to invest time and why. Deep experience leading multi-threaded enterprise deals, navigating executive, technical, and procurement stakeholders with clarity and control is essential. You bring strong commercial acumen and the ability to structure and negotiate deals across pricing, scope, and long-term value. Executive presence and credibility, the ability to communicate with precision, challenge constructively, and earn trust with senior decision-makers are non-negotiable. Experience selling a complex platform, SaaS, fintech, or payments solution into large or operationally sophisticated organisations is required, as is a high standard for disciplined, prepared execution across long and ambiguous sales cycles.

Square, part of Block Inc., offers a remote work environment, medical insurance, flexible time off, retirement savings plans, modern family planning support, and a culture built around empowering you to do the best work of your career while building the life you want. This role will require working across multiple time zones as part of a globally distributed company.

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To apply, share your CV to square@squareup.com
When submitting your application, ensure your CV clearly highlights your years of enterprise sales experience, your track record of exceeding revenue targets, specific examples of complex multi-stakeholder deals you have closed, and your experience selling SaaS, fintech, payments, or platform solutions to large organisations. Your cover letter should explain why you are drawn to the Enterprise Account Executive role at Square and demonstrate your commercial judgement, ownership mindset, and ability to run disciplined enterprise deals at pace. Feel free to forward this opportunity to anyone in your network who may be a strong fit.

About Us:
Square is a cohesive commerce ecosystem launched in 2009 by Block, Inc., consisting of over 30 distinct software, hardware, and financial services products that help sellers start, run, and grow their businesses across payments, banking, payroll, inventory, e-commerce, and more. As of 2024, Square is the US market leader in point-of-sale systems, serving 4 million sellers and processing over USD 228 billion in payments annually, with a presence across the United States, Canada, Japan, Australia, the United Kingdom, Ireland, France, and Spain. Block, Inc., Square's parent company listed on NYSE under the ticker XYZ, builds technology to increase access to the global economy through a portfolio of brands including Square, Cash App, Afterpay, TIDAL, Bitkey, and Proto, collectively serving 57 million users worldwide. Block was founded in 2009 by Jack Dorsey and Jim McKelvey, rebranding from Square, Inc. to Block, Inc. in December 2021 to reflect its expanded mission of economic empowerment across consumers, merchants, artists, and bitcoin participants. Square's enterprise offering serves operationally sophisticated, multi-location sellers across retail, food and beverage, services, and other industries, providing custom integrations, dedicated support, and the full Square ecosystem at scale.