Enterprise Sales Lead

This is a fully remote position, open to applicants in California.

📋 Description

• Lead and nurture a team of Enterprise Account Executives tasked with securing Square's most significant sellers.

• Collaborate with enterprise sales leadership to define Square's future growth trajectory.

• Develop strategic initiatives, elevate execution standards, mentor complex deals, and cultivate a high-performing team.

• Manage the enterprise pipeline, ensuring deal quality, forecasting discipline, and revenue results.

• Create a systematic pipeline-generation process in conjunction with Sales Development, Marketing, and Partnerships.

• Oversee pipeline coverage, generation, new enterprise seller achievements, revenue, and forecasting accuracy.

• Work alongside implementation and account teams to convert signed agreements into successful launches and sustained processing volumes.

• Establish regular rhythms for pipeline assessments, forecasting discussions, account planning, deal evaluations, and performance management.

• Translate enterprise objectives into account and territory strategies while directing team resources toward high-potential prospects.

• Mentor complex deal frameworks and multi-stakeholder sales processes.

• Develop scalable methods for account planning, qualification, discovery, business case formulation, executive engagement, negotiation, and closing.

• Spearhead strategic deals, navigate complex negotiations, foster C-level relationships, and eliminate obstacles.

• Collaborate with Solutions Engineering, Product, Partnerships, Legal, Finance, Marketing, Customer Success, implementation, and sales leadership.

• Integrate customer, competitor, partner, and market insights into product development, pricing, packaging, partnerships, and go-to-market strategies.

⛳️ Requirements

• Over 10 years of enterprise or strategic sales experience, with a proven history of surpassing targets and closing intricate, high-value deals.

• At least 3 years of experience in people leadership, demonstrating success in guiding enterprise teams to achieve revenue goals and in hiring, onboarding, and developing high-performing Account Executives.

• Experience in leading enterprise teams within complex platforms, SaaS, fintech, payments, data, or commerce sectors.

• Proven track record in establishing pipeline-generation strategies, including outbound prospecting, account-based initiatives, and partner-sourced opportunities.

• Demonstrated capability to construct territory, segmentation, and coverage strategies in growing or high-growth markets.

• Extensive experience guiding teams through multifaceted, multi-threaded sales cycles involving executive, technical, procurement, legal, and finance stakeholders.

• Strong commercial insight to coach teams on pricing, negotiation, business case development, deal structuring, and economic considerations.

• Operating and analytical rigor in pipeline management, forecasting, account planning, and deal assessment, with a comfort level in using data to enhance conversion rates and inform resource allocation.

• Possess executive presence and credibility—able to communicate clearly, challenge constructively, and build trust with senior decision-makers.

• Demonstrate technical curiosity and the ability to articulate business value across APIs, integrations, data, automation, and emerging AI applications.

• A focus on customer outcomes, with experience in collaborating across pre-sales, implementation, customer success, product, and support to ensure successful launches for newly acquired enterprise sellers.

• A builder mindset—you thrive in situations of uncertainty, take ownership of results, and are motivated by creating the playbook rather than merely executing an existing one.

🏝️ Benefits

• Remote work options.

• Comprehensive medical insurance.

• Flexible time off policies.

• Retirement savings plans.

• Modern family planning assistance.