Enterprise Sales Lead

Block

. Lead and develop a team of Enterprise Account Executives responsible for winning Square's most strategic sellers .

Posted 11/4/2026full-timeRemote • California • United StatesSenior💰 $319,040 - $478,560 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates extensive experience in enterprise sales leadership, with a strong focus on building high-performing teams, managing complex sales cycles, and driving revenue growth. Proven ability to develop and execute strategic plans, enhance pipeline generation, and foster collaboration across multiple stakeholders.

Highest-signal resume keywords

Enterprise Sales LeadershipComplex Deal NegotiationPipeline Generation StrategiesRevenue ForecastingTeam Development and Coaching

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Enterprise Sales ExperienceSaaS SalesPipeline ManagementAccount PlanningBusiness Case DevelopmentDeal StructuringForecasting DisciplineData AnalysisNegotiation SkillsMarket Strategy Development

Soft Skills

Executive PresenceCommunication SkillsCustomer Outcomes MindsetProblem-SolvingTeam Building

Tools & Technologies

CRM SoftwareSales Analytics ToolsData Management SystemsAPIsAutomation Tools

Industry Keywords

FintechPaymentsCommerceSaaSData Solutions

About the role

Key responsibilities & impact

Lead and develop a team of Enterprise Account Executives responsible for winning Square's most strategic sellers
Partner with enterprise sales leadership to shape Square's next stage of growth
Set strategy, raise execution standards, coach complex deals, and build a high-performing team
Own enterprise pipeline, deal quality, forecast discipline, and revenue outcomes
Build a repeatable pipeline-generation motion with Sales Development, Marketing, and Partnerships
Own pipeline coverage, 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 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 high-potential prospects
Coach complex deal constructs and multi-stakeholder sales cycles
Create scalable approaches to account planning, qualification, discovery, business case development, executive engagement, negotiation, and closing
Lead strategic deals, drive complex negotiations, build C-level relationships, and clear blockers
Collaborate with Solutions Engineering, Product, Partnerships, Legal, Finance, Marketing, Customer Success, implementation, and sales leadership
Bring customer, competitor, partner, and market feedback into product, pricing, packaging, partnerships, and go-to-market strategy

Requirements

What you’ll need

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

Benefits

Comp & perks

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