Head of Square Commercial Operations & Deal Excellence

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.