About this role
Job title: Enterprise Account Executive
About the Role As an Enterprise Account Executive, you will lead Square’s expansion into the country’s most strategic sellers. This high-impact role is for a proven enterprise seller who can identify opportunities, build executive relationships, and drive complex deals from first engagement through launch. You will own accounts end-to-end—setting strategy, generating pipeline, and closing high-value deals across multi-stakeholder buying groups, while partnering with Solutions Engineering, Product, Partnerships, Legal, and Finance to bring the full Square ecosystem to market.
What You'll Do
- Own a targeted set of enterprise accounts
- Set clear priorities and be accountable for pipeline quality, deal progression, and closed revenue across your account set
- Define and execute a clear account strategy
- Focus on the highest-impact opportunities and consistently convert pipeline into high-value wins
- Lead complex, multi-stakeholder deals end-to-end
- Navigate executive, technical, and procurement stakeholders to drive alignment, accelerate decisions, and close deals at pace
- Develop strong, insight-led account POVs
- Translate Square’s platform into differentiated value that advances deals and improves win rates
- Run a disciplined, detail-oriented sales process
- Maintain momentum across long cycles, qualify rigorously, and increase conversion at each stage of the funnel
- Partner cross-functionally to win
- Work across Solutions Engineering, Product, Partnerships, Legal, and Finance to remove blockers and close complex deals effectively
- Represent Square with credibility at senior levels
- Build trusted relationships with executives that unlock access, influence decisions, and drive long-term partnerships
What We're Looking For
- 8+ years of enterprise or strategic sales experience, with a consistent track record of exceeding targets and closing complex, high-value deals with full ownership
- Proven ability to build, qualify, and convert pipeline within a focused account set, with strong judgment on where to invest time and why
- Deep experience leading multi-threaded enterprise deals, navigating executive, technical, and procurement stakeholders with clarity and control
- Strong commercial acumen, with the ability to structure and negotiate deals thoughtfully across pricing, scope, and long-term value
- Executive presence and credibility—you communicate with precision, challenge constructively, and earn trust with senior decision-makers
- Experience selling a complex platform, SaaS, fintech, or payments solution into large or operationally sophisticated organisations
- A high standard for execution: you are disciplined, prepared, and follow through consistently, especially in long and ambiguous sales cycles
- A strong sense of ownership—you take responsibility for outcomes, not just activity, and operate effectively without heavy structure
- The ability to simplify complexity and drive clarity, both externally with customers and internally across teams
Nice to Have
- Experience selling fintech or payments solutions into large or operationally sophisticated organisations