Head of Sales Compensation & Quota Operations

Square Inc.; San Francisco (CA); On-site; USD 218,000 - 327,000; Full time

Job summary

Square, Inc. is seeking a Director, Sales Compensation Operations in San Francisco to own the end-to-end compensation engine across crediting, quotas, and payouts.

You will lead two core functions, build scalable processes, and partner with Sales and Finance leadership to ensure accurate, timely pay. You will manage a team of compensation professionals, optimize data pipelines between Looker, Salesforce, and Pigment, and drive automation to improve accuracy and speed while maintaining strong

Qualifications

• 12+ years in Sales Compensation Operations, Sales Commissions or related field.
• 5+ years of people leadership, building and scaling teams.
• Experience in complex compensation across multiple sales motions and models.
• Hands-on with ICM/sales comp platforms and Salesforce as source system.
• Ability to leverage AI/automation to improve accuracy and speed.
• Strong ETL, data flows between CRM, ICM, and financial systems.
• Advanced Excel/Google Sheets skills; SQL comfort.
• Design and operate controls and audit-ready processes.
• Excellent stakeholder management with Sales, Finance, and Revenue Ops.
• Autonomous in fast-paced environments.

Responsibilities

• Lead, coach, and develop compensation ops teams across multiple functions.
• Oversee monthly and quarterly commission cycles from data through payout.
• Implement crediting rules and quota processes, incl. mid-period adjustments.
• Own data pipelines moving quota, crediting, and revenue between Looker, Salesforce, and Pigment.
• Administer and improve Pigment and Salesforce as core tech stack; drive automation.
• Ensure data quality and audit readiness; maintain controls and documentation.
• Run governance, exception reviews, and policy updates at scale.
• Collaborate with design, quota ops, revenue, finance, and sales leadership.
• Deliver KPIs on payout accuracy, cycle times, and risks; provide insights.
• Help frontline reps understand compensation structures and plans.

Skills

People leadership

Data analysis

Stakeholder management

Automation tools

SQL

ETL pipelines

Excel

Tools

Pigment

Salesforce

Looker

Xactly

CaptivateIQ

Anaplan

Varicent

Job description

Square, Inc. is seeking a Director, Sales Compensation Operations in San Francisco to own the end-to-end compensation engine across crediting, quotas, and payouts.

You will lead two core functions, build scalable processes, and partner with Sales and Finance leadership to ensure accurate, timely pay. You will manage a team of compensation professionals, optimize data pipelines between Looker, Salesforce, and Pigment, and drive automation to improve accuracy and speed while maintaining strong