[Hiring] Enterprise Sales Lead @Block

Role Description

As an Enterprise Sales Lead, US, you will 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. You will be accountable for enterprise pipeline, deal quality, forecast discipline, and revenue outcomes across a focused set of high-value prospects and sellers.

You’ll lead and develop Enterprise Account Executives while staying close to the most strategic opportunities. You’ll partner deeply with Solutions Engineering, Product, Partnerships, Legal, Finance, Marketing, Customer Success, and sales leadership to bring the full Square ecosystem to market.

This is a hands-on people leadership role for someone who has built and scaled high-performing enterprise sales teams in a market where commerce, payments, software, data, and AI are converging.

You Will

• 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.
• Raise talent density and set the performance standard for enterprise selling at Square.
• 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.
• Own pipeline coverage, not only pipeline inspection.
• Deliver new enterprise acquisition outcomes:
• Be accountable for pipeline creation, new enterprise seller wins, revenue, and forecast accuracy.
• Partner with implementation and account teams to turn signed agreements into successful launches and sustained processing volume.
• Establish a rigorous operating cadence:
• Create consistent rhythms for pipeline reviews, forecast calls, account planning, deal inspection, and performance management.
• Hold the team to a high standard of accuracy and preparation in each.
• Own account prioritization and coverage:
• Partner with enterprise sales leadership to translate enterprise priorities into account and territory plans.
• Direct team capacity toward the prospects with the strongest strategic fit and commercial potential.
• Raise the bar on deal execution and deal quality:
• Coach the team through complex deal constructs and multi-stakeholder sales cycles spanning executive, technical, commercial, procurement, legal, and finance stakeholders.
• Hold a high standard on deal economics, implementation feasibility, and commitments Square can deliver.
• Codify repeatable sales motions for upmarket growth:
• Create scalable approaches to account planning, qualification, discovery, business case development, executive engagement, negotiation, and closing.
• Ensure wins become repeatable patterns rather than one-offs.
• 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.
• Build and own trusted relationships with C-level decision-makers.
• Partner cross-functionally to win:
• Work closely with Solutions Engineering, Product, Partnerships, Legal, Finance, Marketing, Customer Success, implementation, and sales leadership to align internal teams around strategic opportunities.
• 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.

Qualifications

• 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.
• 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.
• 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.
• 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.

Benefits

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