Head of Square Commercial Operations & Deal Excellence

Block•Bay Area, CA, United States of America, CA

10h•$239,600 - $359,400•Remote

About The Position

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.

Requirements

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.

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.
Coordinate 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.