Senior Enterprise Sales Leader, US Growth & Strategy

Square; Chicago (IL); On-site; USD 223,000 - 335,000; Full time

Benefits offered by this job

Remote work (flexible)

Medical insurance

Flexible time off

Retirement savings plans

Job summary

Square is seeking an Enterprise Sales Lead, US, to guide a team of Enterprise Account Executives and win Square's most strategic sellers while partnering with enterprise sales leadership to shape our next growth phase.

This leadership role requires coaching high-performing teams, building repeatable sales motions, and owning enterprise pipeline, deal quality, and forecast accuracy across key accounts.

Qualifications

• 10+ years of enterprise or strategic sales experience with a track record of exceeding targets and closing complex deals.
• 3+ years of people leadership, hiring, ramping, and developing Enterprise Account Executives.
• Experience leading enterprise teams in SaaS, fintech, payments, data, or commerce.
• Experience building pipeline-generation motions with outbound, ABM, and partner programs.
• Proven ability to design territory, segmentation, and coverage strategies for high-growth markets.
• Experience guiding multi-stakeholder sales cycles involving exec, technical, procurement, legal, and finance stakeholders.
• Strong pricing, negotiation, and deal-structure skills with data-driven decision making.
• Executive presence and credibility with senior decision-makers and cross-functional partners.

Responsibilities

• Build and coach a high-performing enterprise team with clear expectations and accountability.
• Generate enterprise pipeline via outbound, marketing, and partnerships with strong coverage.
• Deliver new enterprise wins, revenue, and forecast accuracy; coordinate launches.
• Establish rigorous operating cadence for pipeline reviews, forecasting, and deal inspection.
• Own account prioritization and coverage aligned with strategic opportunities.
• Raise the bar on deal quality through coaching on complex, multi-stakeholder deals.
• Codify scalable upmarket sales motions for repeatable wins at scale.
• Lead top-priority deals from the front with executive-level engagement and blockers removal.

Skills

Enterprise sales leadership

People leadership

SaaS/fintech/payments experience

Pipeline generation

Account planning

Executive relationship management

Data-driven decision making

Deal coaching

Job description

Square is seeking an Enterprise Sales Lead, US, to guide a team of Enterprise Account Executives and win Square's most strategic sellers while partnering with enterprise sales leadership to shape our next growth phase.

This leadership role requires coaching high-performing teams, building repeatable sales motions, and owning enterprise pipeline, deal quality, and forecast accuracy across key accounts.