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.

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