Director, Sales Compensation Operations

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

2d•$217,800 - $326,800•Remote

About The Position

Since opening its doors in 2009, Square (now Block) has evolved significantly, expanding from payment processing to integrated, omnichannel solutions for sellers. These solutions cover online sales, inventory management, buy now, pay later functionality, appointment booking, customer engagement, and staff management. Financial services tools are embedded at the point of sale, providing merchants with access to business loans and cash flow management. Afterpay further enhances Square's goal of providing omnichannel tools that drive growth and enable sellers to compete at a larger scale. Block partners with sellers of all sizes, from large enterprises to small businesses, and offers solutions that grow with its customers. The company is focused on building a significant, meaningful, and lasting business while helping sellers worldwide do the same.

Requirements

12+ years of experience in Sales Compensation Operations, Sales Commissions, Revenue Operations, or a related field.
5+ years of people leadership experience, with a track record of building, coaching, and scaling high-performing operations teams.
Experience operating complex compensation environments across multiple sales motions, roles, and revenue models.
Expertise administering an ICM / sales compensation platform (Pigment strongly preferred; Xactly, CaptivateIQ, Anaplan, Varicent, or similar) and strong hands-on comfort with Salesforce as a source system.
Demonstrated ability to leverage AI and automation tools to accelerate and improve the accuracy of calculation, reconciliation, reporting, and operational workflows.
Strong understanding of ETL pipelines and data flows between CRM, ICM, and financial systems.
Advanced Excel / Google Sheets skills and comfort with SQL.
Strong analytical and problem-solving ability.
Demonstrated ability to design and operate controls, documentation, and audit-ready processes.
Excellent stakeholder management and communication skills, with experience partnering with Sales, Finance, and Revenue Operations leadership.
Ability to operate autonomously in a fast-paced environment where priorities shift.

Nice To Haves

Experience in payments, fintech, or a consumption-based business model.
Hands-on experience building or directly managing ETL pipelines between comp systems.
Experience migrating or implementing a commissions platform.

Responsibilities

Lead, coach, and develop a team across business operations, crediting operations, data pipeline management, data quality and audit, process governance, and commission calculation.
Oversee the end-to-end monthly and quarterly commission cycle, from crediting and quota data through calculation, validation, review, approval, and payout.
Implement and operationalize the crediting rules and processes, including quota issuance and rollup, executing credit rules, and processing mid-period adjustments.
Own the data pipelines that move quota, crediting, and revenue data between systems like Looker, Salesforce, and Pigment, maintaining transformation logic and resolving data issues.
Administer and improve the sales compensation tech stack, including Pigment for ICM and quota issuance, and Salesforce as the system of record, driving automation, data integrity, and scalability.
Own data quality and audit for commissionable crediting data, ensuring source data accuracy, maintaining controls, documentation, and audit readiness.
Run process governance, exception review, and policy review, handling edge cases at scale and fixing root causes of recurring issues.
Partner with Sales Compensation Design, Quota Operations, Revenue Operations, Finance, and Sales leadership to translate plan design into execution, support plan rollouts, and provide operational feedback.
Deliver reporting and insights on payout accuracy, cycle times, exceptions, and other operational KPIs, flagging risks and prioritizing improvements.
Enable frontline sales teams to understand their compensation structures and plans to build trust and transparency.