Head of Square Commercial Operations & Deal Excellence

About the role

You will own the end-to-end commercial operating system for Square's global Revenue organization, setting the standard for how deals are won, managed, and optimized at scale. In this role, you will serve as the central architect of pricing integrity, deal governance, and commercial strategy, ensuring all motions are aligned with financial outcomes. You will bridge the gap between Sales, Finance, and Product teams, translating high-level objectives into executable frameworks that every team can follow. By establishing clear playbooks and decision-support tools, you will remove ambiguity for sellers and empower them to act with speed and confidence. You will lead the modernization of commercial processes, leveraging AI and automation to eliminate manual work and drive quote-to-cash efficiency. This position requires deep financial rigor to evaluate tradeoffs, model profitability, and ensure that every decision supports sustainable growth. You will mentor a global team of commercial operations professionals, elevating their expertise and creating a culture of excellence and accountability. Ultimately, you will be the executive-level advisor guiding complex negotiations and shaping the commercial narrative for Block's most strategic customers.

Key facts

What you'll do

Partner with Finance to translate pricing strategy into scalable frameworks, playbooks, and decision-support tools that sellers can use every day.

Manage global Deal Desk operations, including intake workflows, approval matrices, and discount governance to ensure consistent and compliant execution.

Lead commercial strategy for high-value strategic customer opportunities and advise executive leadership on complex negotiations and tradeoffs.

Modernize commercial processes by integrating AI and automation into seller workflows to improve quote-to-cash efficiency and reduce manual errors.

Establish reporting and dashboards to monitor deal cycle times, margin realization, and pricing performance, turning data into actionable insight.

Build and mentor a global team focused on commercial excellence, providing coaching, clear expectations, and career development.

Define and implement pricing and packaging strategies that optimize revenue without compromising market competitiveness or win rates.

Own the end-to-end deal governance process, identifying bottlenecks and designing solutions that accelerate decision-making and reduce friction.

Collaborate with Product and Sales leaders to align commercial objectives with product positioning, packaging, and market entry strategies.

Drive the adoption of standardized playbooks and tools across regions, ensuring that best practices are scaled globally.

Evaluate the performance of commercial policies and adjust them based on market feedback, results, and changing business conditions.

Partner with legal and compliance to ensure that all deal structures and terms meet regulatory requirements and internal risk standards.

Champion data-driven decision-making by building the metrics and stories that clearly link commercial activities to financial outcomes.

Act as the primary point of contact for executive sponsors on commercial operations, providing concise, high-impact updates and recommendations.

Requirements

• 10+ years of experience in Deal Desk, Commercial Operations, Revenue Operations, Sales Strategy, Pricing, or consulting, with a proven ability to deliver results in complex environments.
• Proven track record of scaling commercial operating systems within fintech, SaaS, payments, or enterprise software, demonstrating comfort with high growth and ambiguity.
• Expertise in enterprise sales, complex deal structuring, and commercial governance, including the design and oversight of policies that protect the business.
• Strong financial acumen with the ability to evaluate commercial tradeoffs and profitability, ensuring that decisions support long-term value creation.
• Demonstrated success in building scalable approval workflows and AI-enabled processes that improve speed, accuracy, and consistency.
• Exceptional cross-functional leadership skills with the ability to influence executive stakeholders, even in the absence of direct authority.
• Experience operating in a matrixed organization where you must align Sales, Finance, Product, and Legal around shared commercial objectives.
• Comfort with data, metrics, and analytical tools, using insights to drive continuous improvement and validate the impact of operational changes.
• Excellent written and verbal communication skills, with the ability to translate complex concepts into clear, actionable guidance for diverse audiences.
• A builder's mindset, with the curiosity to test new tools, challenge existing processes, and iterate based on feedback and results.
• Commitment to ethical decision-making and compliance, ensuring that all commercial activities adhere to the highest standards of integrity.
• Demonstrated ability to manage multiple priorities in a fast-paced environment while maintaining attention to detail and delivering on commitments.
• Willingness to travel occasionally to support key initiatives, partner teams, and engage with customers in strategic market discussions.

Skills & tools

Commercial strategy and pricing operations that balance growth with profitability and risk management.

Enterprise deal structuring and governance, including the design of approval workflows and exception handling.

AI and automation for sales workflows, including the evaluation and implementation of tools that enhance seller productivity.

Financial modeling and analytical reporting, with the ability to build dashboards that clarify performance and guide action.

Cross-functional stakeholder management, including the ability to build trust and align incentives across diverse teams.

Practical notes

Block utilizes a market-based pay approach with four geographic zones, and compensation is set within a zone based on location and experience.

Candidates may submit up to 9 active applications within a 60-day period, providing flexibility in how you manage your job search.

Reapplications for the same role are permitted 90 days after a previous review, allowing time for new experiences or qualifications to strengthen your application.

The company may use AI tools to assist in the evaluation of job applications, screening communications, and supporting hiring decisions.

Benefits include medical insurance, retirement savings, flexible time off, and family planning support, contributing to a comprehensive total rewards package.