Head of Square Commercial Operations & Deal Excellence

It all started with an idea at Block in 2013. Initially built to take the pain out of peer-to-peer payments, Cash App has gone from a simple product with a single purpose to a dynamic ecosystem, developing unique financial products, including Afterpay/Clearpay, to provide a better way to send, spend, invest, borrow and save to our 50+ million monthly active customers. We want to redefine the world’s relationship with money to make it more relatable, instantly available, and universally accessible.

Today, Cash App has thousands of employees working globally across office and remote locations, with a culture geared toward innovation, collaboration and impact. We’ve been a distributed team since day one, and many of our roles can be done remotely from the countries where Cash App operates. No matter the location, we tailor our experience to ensure our employees are creative, productive, and happy.

About the Role:

As Square continues to scale globally, our commercial engine is becoming increasingly complex. We serve sellers across multiple markets, products, customer segments, and sales channels, requiring faster and more consistent decisions around pricing, commercial investments, and deal execution.

We’re hiring a Head of Square Commercial Operations & Deal Excellence to build and lead the commercial operating system that powers Square’s global Revenue organization.

This team sits within Revenue and serves as the connective tissue between Sales, Finance, Product, Engineering, Legal, Risk, and Revenue Operations. Finance owns Square’s pricing principles, profitability objectives, investment frameworks, and commercial guardrails. This team operationalizes those guardrails—building the processes, tools, governance, and strategic support that enable sellers to move faster while protecting long-term business value.

This leader will own Square’s global Deal Desk, pricing operations, strategic deal support, commercial governance, and commercial operations. Their mission is simple: enable Square to win more business by making every commercial decision faster, smarter, and more consistent.

What You’ll Own:

Commercial Strategy & Operations

• Partner with Finance to operationalize Square’s pricing strategy, commercial policies, and investment guardrails.
• Translate pricing strategy into scalable seller workflows, pricing frameworks, playbooks, calculators, and decision-support tools.
• Continuously improve how pricing decisions are executed across products, customer segments, markets, and sales channels.
• Bring market insights, competitive intelligence, and field feedback back into pricing strategy and product packaging.

Strategic Deal Excellence

• Lead commercial strategy for Square’s largest and most strategic customer opportunities.
• Partner with enterprise sales leaders to structure creative commercial solutions within established pricing and investment guardrails.
• Advise executive leadership on complex commercial decisions, non-standard pricing, and strategic investments.
• Coordinate executive reviews and cross-functional approvals for high-value commercial opportunities.

Global Deal Desk

• Own the end-to-end operation of Square’s global Deal Desk.
• Build scalable intake, review, approval, and booking workflows that reduce friction for sellers.
• Establish SLAs and operating rhythms that ensure pricing and approvals never become bottlenecks.
• Design repeatable playbooks that eliminate unnecessary manual reviews through standardized commercial patterns.
• Own approval matrices, exception management, discount governance, and escalation processes across Square globally.

Commercial Operations & Automation

• Modernize Square’s commercial operating model through AI and automation.
• Embed pricing recommendations, approval logic, and commercial guardrails directly into seller workflows.
• Simplify quote-to-cash processes and improve the overall seller experience.
• Increase deal velocity without sacrificing governance or profitability.

Commercial Insights & Governance

• Monitor pricing performance, approval trends, discount behavior, deal cycle time, and margin realization.
• Identify opportunities to improve commercial performance, seller productivity, and profitability.
• Build executive dashboards and reporting that provide visibility into Square’s commercial health.
• Partner with Finance, Legal, Product, and Risk to continuously evolve Square’s commercial governance framework.

Leadership

• Build and lead a high-performing global team spanning Deal Desk, pricing operations, strategic deal support, and commercial excellence.
• Develop exceptional talent and foster a culture of operational excellence, customer obsession, and continuous improvement.
• Build trusted partnerships across Revenue, Finance, Product, Legal, Engineering, and Risk.

What We’re Looking For:

• 10+ years of experience leading Deal Desk, Commercial Operations, Revenue Operations, Sales Strategy, Pricing, Consulting, or related functions.
• Experience building and scaling commercial operating systems within SaaS, fintech, payments, or enterprise software.
• Deep expertise in enterprise sales, pricing operations, commercial governance, and complex deal structuring.
• Strong commercial judgment with experience supporting high-value strategic negotiations.
• Proven ability to build scalable operating models, approval workflows, and AI-enabled commercial processes.
• Strong analytical and financial acumen with the ability to evaluate complex commercial tradeoffs.
• Exceptional cross-functional leadership and executive influence.

Success in This Role

Within your first year, you will have:

• Built the commercial operating system that enables Square’s Revenue organization to move faster while maintaining commercial discipline.
• Reduced deal cycle times through streamlined workflows and AI-enabled automation.
• Increased consistency in pricing execution and commercial decision-making across every Square market.
• Established a world-class Deal Desk that supports both routine and strategic commercial opportunities.
• Improved seller productivity through better tools, clearer guidance, and simpler commercial processes.
• Become a trusted commercial partner to Sales, Finance, Product, and executive leadership.

We’re working to build a more inclusive economy where our customers have equal access to opportunity, and we strive to live by these same values in building our workplace. Block is an equal opportunity employer evaluating all employees and job applicants without regard to identity or any legally protected class. We will consider qualified applicants with arrest or conviction records for employment in accordance with state and local laws and “fair chance” ordinances.

We believe in being fair, and are committed to an inclusive interview experience, including providing reasonable accommodations to disabled applicants throughout the recruitment process. We encourage applicants to share any needed accommodations with their recruiter, who will treat these requests as confidentially as possible. Want to learn more about what we’re doing to build a workplace that is fair and square? Check out our I+D page.