Enterprise Sales Lead, US

Block•San Francisco, CA

9d•$223,328 - $334,992

About The Position

The Enterprise Sales Lead, US will lead and develop a team of Enterprise Account Executives responsible for winning Square’s most strategic sellers, while partnering with enterprise sales leadership to shape the next stage of growth. This hands-on leadership role owns enterprise pipeline, deal quality, forecast discipline, and revenue outcomes across high-value prospects and sellers. The leader will set strategy, coach complex deals, establish execution standards, and build a high-performing team in a market where commerce, payments, software, data, and AI are converging. The role partners closely with Solutions Engineering, Product, Partnerships, Legal, Finance, Marketing, Customer Success, implementation, and sales leadership to bring Square’s ecosystem to market. It includes leading strategic opportunities directly, building repeatable upmarket sales motions, and sharing market insight to inform product, pricing, packaging, partnerships, and go-to-market strategy.

Requirements

10+ years of enterprise or strategic sales experience, including a strong record of exceeding targets and closing complex, high-value deals.
3+ years of people leadership experience, with a record of leading enterprise teams to revenue targets and hiring, ramping, and developing successful Account Executives.
Experience leading enterprise teams in complex platform, SaaS, fintech, payments, data, or commerce environments.
Experience building pipeline-generation motions, including outbound prospecting, account-based programs, and partner-sourced opportunities.
Ability to build territory, segmentation, and coverage strategies in a developing or high-growth market.
Deep experience leading multi-threaded sales cycles involving executive, technical, procurement, legal, and finance stakeholders.
Commercial acumen in pricing, negotiation, business case development, deal structure, and deal economics.
Operating and analytical discipline in pipeline management, forecasting, account planning, and deal inspection, with ability to use data to improve conversion and make resource decisions.
Executive presence and credibility, with precise communication, constructive challenge, and ability to earn senior decision-makers’ trust.
Technical curiosity and ability to sell business value across APIs, integrations, data, automation, and emerging AI use cases.
Customer outcomes mindset and experience partnering across pre-sales, implementation, customer success, product, and support to set newly won enterprise sellers up for successful launches.
Builder mentality, including taking ownership, creating clarity in ambiguity, and developing playbooks.

Responsibilities

Hire, develop, and lead Enterprise Account Executives through clear expectations, deal coaching, pipeline inspection, feedback, and accountability.
Build a repeatable enterprise pipeline-generation motion with Sales Development, Marketing, and Partnerships, including outbound prospecting, executive engagement, and account-based programs.
Own pipeline coverage and deliver new enterprise seller wins, revenue, and forecast accuracy.
Partner with implementation and account teams to support successful launches and sustained processing volume after agreements are signed.
Establish operating rhythms for pipeline reviews, forecast calls, account planning, deal inspection, and performance management.
Translate enterprise priorities into account and territory plans and direct team capacity toward prospects with the strongest strategic fit and commercial potential.
Coach complex, multi-stakeholder sales cycles and maintain high standards for deal economics, implementation feasibility, and deliverable commitments.
Develop scalable approaches to account planning, qualification, discovery, business case development, executive engagement, negotiation, and closing.
Lead the most strategic pursuits by setting account strategy, engaging executives, driving negotiations, clearing blockers, and building trusted C-level relationships.
Coordinate cross-functional teams to align around strategic opportunities and advance deals.
Bring customer, competitor, partner, and market feedback into Square to influence product, pricing, packaging, partnerships, and go-to-market strategy.