Head of Square Commercial Operations & Deal Excellence
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.
Responsibilities
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.
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.
Cook up executive reviews and cross-functional approvals for high-value commercial opportunities.
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.
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.
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.
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.
Qualifications
10+ years of experience leading Deal Desk, Commercial Operations, Revenue Operations, Sales Strategy, Pricing, Consulting, or related functions.
Deep expertise in enterprise sales, pricing operations, commercial governance, and complex deal structuring.
Strong commercial judgment with experience supporting high-value strategic negotiations.
Prior experience building and scaling commercial operating systems within SaaS, fintech, payments, or enterprise software.
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.
Benefits
No benefits section provided in the job posting.
Pay
No pay range provided in the job posting.
Schedule
No schedule information provided in the job posting.