Director, Sales Compensation Operations

Since we opened our doors in 2009, the world of commerce has evolved immensely, and so has Square. After enabling anyone to take payments and never miss a sale, we saw sellers stymied by disparate, outmoded products and tools that wouldn’t work together.

So we expanded into software and started building integrated, omnichannel solutions – to help sellers sell online, manage inventory, offer buy now, pay later functionality, book appointments, engage loyal buyers, and hire and pay staff. Across it all, we’ve embedded financial services tools at the point of sale, so merchants can access a business loan and manage their cash flow in one place. Afterpay furthers our goal to provide omnichannel tools that unlock meaningful value and growth, enabling sellers to capture the next generation shopper, increase order sizes, and compete at a larger scale.

Today, we are a partner to sellers of all sizes – large, enterprise-scale businesses with complex operations, sellers just starting, as well as merchants who began selling with Square and have grown larger over time. As our sellers grow, so do our solutions. There is a massive opportunity in front of us. We’re building a significant, meaningful, and lasting business, and we are helping sellers worldwide do the same.

The Role

We are looking for a Director, Sales Compensation Operations to own the end-to-end operational engine behind how our go-to-market teams are credited, assigned quotas, and paid. This is a people-leadership role at the center of Sales, Finance, Revenue Operations, and Systems, where accuracy, timeliness, and trust are everything.

You will lead two core functions — crediting & quota operations and commission operations — ensuring every rep understands how they are measured and is paid correctly and on time.

You'll lead and grow a team of compensation operations professionals, setting the operating rhythm for how compensation runs at scale. You'll build repeatable processes and controls, drive automation where it improves accuracy and speed, and partner closely with senior Sales and Finance leadership to make sure our incentive programs are executed accurately. You will report to the Head of Revenue Strategy & Planning within the Revenue organization.

You Will

• Lead, coach, and develop a team across business operations, crediting operations, data pipeline management, data quality and audit, process governance, and commission calculation. Set clear goals and operating cadences, invest in career growth, and get into the details when the work calls for it.
• Oversee the end-to-end monthly and quarterly commission cycle, from crediting and quota data through calculation, validation, review, approval, and payout. Make sure comp plan policies are implemented accurately and every rep is paid correctly and on time.
• Implement and operationalize the crediting rules and processes behind them. This includes quota issuance and rollup to leaders by role, executing credit rules, and processing mid-period adjustments across the go-to-market organization.
• Own the data pipelines that move quota, crediting, and revenue data between systems such as Looker, Salesforce, and Pigment. Maintain the transformation logic that powers them, and research and resolve data issues when they arise.
• Administer and improve our sales compensation tech stack: Pigment for ICM and quota issuance, and Salesforce as our system of record. Drive automation, data integrity, and scalability as the business grows.
• Own data quality and audit for commissionable crediting data. Cure and reconcile source data before it feeds calculations. Maintain controls, documentation, and audit readiness.
• Run process governance, exception review, and policy review. Handle edge cases at scale without creating a backlog. Identify what's breaking repeatedly and fix the root cause.
• Partner with Sales Compensation Design, Quota Operations, Revenue Operations, Finance, and Sales leadership. Translate plan design into execution, support the rollout and validation of new and updated plans, and bring operational feedback into future design decisions.
• Deliver reporting and insights on payout accuracy, cycle times, exceptions, and other operational KPIs. Flag risks early and use data to prioritize improvements.
• Enable frontline sales teams to understand their compensation structures and plans, including how they are credited, measured, and paid, to build trust and transparency in the incentive program.

You Have

• 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.

Bonus

• Experience in payments, fintech, or a consumption-based business model.
• Hands-on experience building or directly managing ETL pipelines between comp systems.
• You've migrated or implemented a commissions platform before.

We're working to build a more inclusive economy where our customers have equal access to opportunity, and we strive to live by these same values in building our workplace. Block is an equal opportunity employer evaluating all employees and job applicants without regard to identity or any legally protected class. We will consider qualified applicants with arrest or conviction records for employment in accordance with state and local laws and “fair chance” ordinances. We believe in being fair, and are committed to an inclusive interview experience, including providing reasonable accommodations to disabled applicants throughout the recruitment process. We encourage applicants to share any needed accommodations with their recruiter, who will treat these requests as confidentially as possible. Want to learn more about what we're doing to build a workplace that is fair and square? Check out our I+D page.