# Head of Square Commercial Operations & Deal Excellence

**Company:** [Square](https://hotfix.jobs/companies/square)
**Location:** California
**Role:** Revenue Operations
**Salary:** $240k – $359k/yr
**Experience:** 10+ years
**Skills:** commercial operations, deal desk, pricing operations, Revenue Operations, Sales Strategy, Enterprise Sales, commercial governance, complex deal structuring, AI Automation, financial acumen, Cross-Functional Leadership
**Posted:** 2026-07-16

> Lead Square's global commercial operating system as Head of Commercial Operations & Deal Excellence. Own Deal Desk, pricing operations, strategic deal support, governance, and AI-driven automation to accelerate revenue decisions while protecting profitability. Requires 10+ years leading commercial ops in SaaS/fintech/payments with deep expertise in enterprise deal structuring and executive influence.

## Job Description

## 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.

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