Enterprise Sales Lead, US

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

Since we opened our doors in 2009, the world of commerce has evolved immensely, and so has Square. After enabling anyone to take payments and never miss a sale, we saw sellers stymied by disparate, outmoded products and tools that wouldn’t work together.

So we expanded into software and started building integrated, omnichannel solutions – to help sellers sell online, manage inventory, offer buy now, pay later functionality, book appointments, engage loyal buyers, and hire and pay staff. Across it all, we’ve embedded financial services tools at the point of sale, so merchants can access a business loan and manage their cash flow in one place. Afterpay furthers our goal to provide omnichannel tools that unlock meaningful value and growth, enabling sellers to capture the next generation shopper, increase order sizes, and compete at a larger scale.

Today, we are a partner to sellers of all sizes – large, enterprise-scale businesses with complex operations, sellers just starting, as well as merchants who began selling with Square and have grown larger over time. As our sellers grow, so do our solutions. There is a massive opportunity in front of us. We’re building a significant, meaningful, and lasting business, and we are helping sellers worldwide do the same.

The Role

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'll bring the judgment of an experienced sales leader, the technical curiosity to sell a platform, and the operating discipline to turn an emerging motion into a repeatable business.

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, and 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, and 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, then 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, so 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, and make the case for Square yourself when the deal demands it.
• 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, and move deals forward.
• 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.

You Have

• 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

Block takes a market-based approach to pay, and pay may vary depending on your location. U.S. locations are categorized into one of four zones based on a cost of labor index for that geographic area. The successful candidate’s starting pay will be determined based on job-related skills, experience, qualifications, work location, and market conditions. These ranges may be modified in the future.To find a location’s zone designation, please refer to thisresource. If a location of interest is not listed, please speak with a recruiter for additional information.

Zone A:: $223,328 USD - $334,992 USD

Zone B: : $223,328 USD - $334,992 USD

Zone C:: $223,328 USD - $334,992 USD

Zone D:: $223,328 USD - $334,992 USD

Use of AI in Our Hiring Process

We may use automated AI tools to evaluate job applications for efficiency and consistency. These tools comply with local regulations, including bias audits, and we handle all personal data in accordance with state and local privacy laws.

Every benefit we offer is designed with one goal: empowering you to do the best work of your career while building the life you want. Remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning are just some of our offering.

Check out our other benefits at Block.

Block, Inc. (NYSE: XYZ) builds technology to increase access to the global economy. Each of our brands unlocks different aspects of the economy for more people.Square makes commerce and financial services accessible to sellers.Cash App is the easy way to spend, send, and store money.Afterpay is transforming the way customers manage their spending over time.TIDAL is a music platform that empowers artists to thrive as entrepreneurs.Bitkey is a simple self-custody wallet built for bitcoin.Proto is a suite of bitcoin mining products and services. Together, we’re helping build a financial system that is open to everyone.

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