Enterprise Sales Lead, US
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 this resource. If a location of interest is not listed, please speak with a recruiter for additional information.
Application Guidelines
Candidates may submit up to 9 active applications within a 60-day period. Reapplications to the same role are accepted 90 days after a previous application has been reviewed.
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.
Contact us here with hiring practice or data usage questions.
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.
Privacy Policy
Skills
As published by greenhouse · 16 questions · 2 written answers
Basics
First Name, Last Name, Email, Phone, Resume/CV, Cover Letter, Location
Short answers (7)
- LinkedIn Profile optional
- Additional profiles (e.g. GitHub, Stack Overflow) optional
- If you answered "Yes" to the question above, please enter your dates of employment. Note that your performance history may be reviewed as part of the application process. optional
- If you answered "Yes" to the question above, please enter your dates of contract engagement or work through agency. optional
- I certify that all of the information I have provided is correct and complete and realize that falsification or misrepresentation, including omission, on this or any other personnel record, or in the hiring process, may be grounds for refusal of employment, or if hired, may lead to disciplinary action, up to and including termination. By signing this Electronic Signature Acknowledgment Online Form, I agree that my electronic signature is the legally binding equivalent to my handwritten signature. Whenever I execute an electronic signature, it has the same validity and meaning as my handwritten signature. I will not, at any time in the future, repudiate the meaning of my electronic signature or claim that my electronic signature is not legally binding. Please sign by typing your Full Legal First, Middle Initial, and Last Name.
- What is your Legal First Name?
- What is your Legal Last Name?
Pick from a list (7)
- Will you now or in the future require sponsorship for work authorization? (This information will not be used in assessing your qualifications for any position.)
- Are you authorized to work lawfully in the location posted for this position?
- Have you ever been employed full-time at Block or its subsidiaries?
- Have you ever provided any contract work for Block, Inc. or any of its subsidiaries or affiliates (whether in the U.S. or internationally)?
- By clicking “accept,” you agree that any disputes related to your application, including those related to Block’s selection process, hiring decision, and your background check, shall be submitted to binding arbitration with the Judicial Arbitration and Mediation Services, Inc. (JAMS) on an individual basis only in San Francisco, before a single arbitrator according to the applicable JAMS Rules then in effect, with Block bearing all costs unique to arbitration. To the extent permitted by law, you and Block each waive the right to initiate or participate in any class, collective, or representative action against the other in any forum (including court and arbitration). If any provision of this agreement is deemed unenforceable, the remainder shall remain in effect, except that, notwithstanding the above, under no circumstances shall class or collective, or representative proceedings be permitted in arbitration.
- How we interview: Our hiring process prioritizes authenticity and fairness, and we ask all candidates to adhere to a few key expectations. Acceptable use of AI may differ depending on the role, so we encourage you to confirm with your recruiter what is or isn’t permitted during the process. Recording any part of the interview without consent is prohibited. However, if you need recording as an accommodation, please notify your recruiter before your scheduled interview. During virtual interviews, keep your video on to foster meaningful engagement; if you require accommodations, please inform our team in advance. Lastly, maintain confidentiality by refraining from sharing any proprietary or trade secret information from previous employers or other sources throughout the interview process.
- With your permission, we may use AI transcription software to transcribe and summarize your interview to help us capture accurate notes. Participation is entirely voluntary, and your decision will not affect the outcome of your application. You can withdraw consent at any time. Do you consent to us using AI to transcribe and summarize your interview?
Written answers (2)
- Tell us a bit about why you're applying to work here. What excited you about this role? optional
- Block's purpose is economic empowerment. Briefly tell us about what that purpose means to you. optional