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About the Role

Lead and develop a team of Enterprise Account Executives responsible for winning Square's most strategic sellers and partner with enterprise sales leadership to shape our next stage of growth. This is a leadership role for a proven enterprise sales leader who can set strategy, raise execution standards, coach complex deals, and build a high-performing team.

Responsibilities

Build and coach a high-performing enterprise team: Hire, develop, and lead Enterprise Account Executives through clear expectations, deal coaching, pipeline inspection, direct feedback, and accountability for results.
Generate enterprise pipeline: Build a repeatable pipeline-generation motion with Sales Development, Marketing, and Partnerships, combining targeted outbound prospecting, executive engagement, and account-based programs.
Deliver new enterprise acquisition outcomes: Be accountable for pipeline creation, new enterprise seller wins, revenue, and forecast accuracy.
Establish a rigorous operating cadence: Create consistent rhythms for pipeline reviews, forecast calls, account planning, deal inspection, and performance management.
Own account prioritization and coverage: Partner with enterprise sales leadership to translate enterprise priorities into account and territory plans.
Raise the bar on deal execution and deal quality: Coach the team through complex deal constructs and multi-stakeholder sales cycles.
Codify repeatable sales motions for upmarket growth: Create scalable approaches to account planning, qualification, discovery, business case development, executive engagement, negotiation, and closing.
Lead the most strategic deals from the front: Set account strategy, open executive doors, drive complex negotiations, and clear blockers on the highest-priority pursuits.
Partner cross-functionally to win: Work closely with Solutions Engineering, Product, Partnerships, Legal, Finance, Marketing, Customer Success, implementation, and sales leadership.
Turn market insight into business impact: Bring customer, competitor, partner, and market feedback back into Square to influence product, pricing, packaging, partnerships, and go-to-market strategy.

Requirements

10+ years of enterprise or strategic sales experience, including a strong track record of exceeding targets and closing complex, high-value deals
3+ years of people leadership experience, with a demonstrated record of leading enterprise teams to hit revenue targets and of hiring, ramping, and developing Account Executives who perform
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
Proven ability to build territory, segmentation, and coverage strategies in a developing or high-growth market
Deep experience leading teams through complex, multi-threaded sales cycles involving executive, technical, procurement, legal, and finance stakeholders
Commercial acumen to coach teams on pricing, negotiation, business case development, deal structure, and deal economics
Operating and analytical discipline across pipeline management, forecasting, account planning, and deal inspection, with comfort using data to improve conversion and make resource decisions
Executive presence and credibility—you communicate with precision, challenge constructively, and earn trust with senior decision-makers
Technical curiosity and the ability to sell business value across APIs, integrations, data, automation, and emerging AI use cases
A customer outcomes mindset, with experience partnering across pre-sales, implementation, customer success, product, and support to set newly won enterprise sellers up for a successful launch
A builder mentality—you create clarity in ambiguity, take ownership of outcomes, and are energized by building the playbook, not just running an existing one

Skills

Enterprise Sales
People Leadership
Sales Strategy
Deal Coaching
Pipeline Generation
Outbound Prospecting
Account-Based Marketing
Revenue Outcomes
Forecast Accuracy
Operating Cadence
Territory Planning
Deal Execution
Sales Cycle Management
Negotiation
Business Case Development
Executive Engagement
Cross-functional Partnership
Market Insight Analysis
Platform Sales
SaaS Sales
Fintech
Payments
Data Analysis
AI Use Cases
Customer Success
Product Strategy

Location

Work Type

Remote

Experience Level

10+ years of enterprise or strategic sales experience
3+ years of people leadership experience

Salary/Compensations

$223,328—$334,992 USD (Zone A)
$223,328—$334,992 USD (Zone B)
$223,328—$334,992 USD (Zone C)
$223,328—$334,992 USD (Zone D)

Benefits

Remote work
Medical insurance
Flexible time off
Retirement savings plans
Modern family planning

About the Company

Block, Inc. (NYSE: XYZ) builds technology to increase access to the global economy.
Square makes commerce and financial services accessible to sellers.
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Together, we’re helping build a financial system that is open to everyone.