Order to Cash, Order Management and Billing Lead

About the Team

OpenAI Finance ensures the organization is positioned for long‑term success as we pursue our mission.

The Order to Cash (OTC) team oversees the complete flow of commercial transactions from order intake and provisioning through billing, collections, and cash application — ensuring accuracy, compliance, and operational excellence in support of OpenAI’s mission to ensure artificial general intelligence benefits all of humanity.

We are looking for a strategic and hands‑on leader to own and scale the Order Management and Billing Operations function within our OTC organization. This role is responsible for designing and operating the end‑to‑end order‑to‑invoice lifecycle, ensuring that contract, provisioning, and pricing data flow seamlessly through our systems to produce accurate, timely, and audit‑ready billing. You will shape our operational strategy, partner closely across Revenue Systems, Engineering, and GTM teams, and build the operational backbone that will support the next phase of OpenAI’s scale and evolution.

This is a hands‑on leadership role that blends operational execution with strategic process design, cross‑functional collaboration, and system optimization—critical for scaling our OTC function to support rapid growth and global operations.

This role is based in San Francisco, CA. We use a hybrid work model of 3 days in the office per week and offer relocation assistance to new employees.

• Oversee the complete order‑to‑invoice lifecycle and establish the systems, controls, and workflows needed to ensure accurate, timely, and audit‑ready billing at scale.
• Embed AI and automation directly into Order Management and Billing workflows to reduce rework, eliminate manual intervention, and proactively identify discrepancies before they become billing or revenue impacting issues.
• Partner cross‑functionally with Revenue Systems, Product, Engineering, GTM, Legal, and Deal Desk to ensure quoting, configuration, provisioning, billing, and ERP stay aligned and integrated as new products and pricing models launch.
• Build and enforce controls and segregation of duties, ensuring documentation, approvals, reconciliations, and exception handling are clear, repeatable, and audit ready.
• Lead Order to Cash representation in system implementations and enhancements, defining requirements, validating data flows, and ensuring new capabilities support both current needs and long‑term scalability.
• Ensure data completeness and accuracy during month end close by validating that all order, pricing, billing, and usage information is fully captured and reconciled before flowing into revenue systems.
• Build and lead a high performance team, creating role clarity, mentoring talent, setting accountability mechanisms, and fostering a culture of ownership, transparency, and continuous improvement.
• Establish KPIs and performance dashboards that measure billing accuracy, cycle times, automation rates, customer escalations, and overall operational throughput to guide decision‑making and prioritization.
• Develop and maintain operational documentation (SOPs, playbooks, runbooks, training pathways) to support consistent execution and team scalability.

• 10+ years of experience across Order‑to‑Cash, Order Management, and Billing Operations within a SaaS, enterprise software, or high‑growth technology environment, including at least 5 years of proven leadership in a managerial role.
• In‑depth knowledge of SaaS billing models, including subscription, usage‑based, and hybrid structures.
• Hands‑on experience with CPQ, ERP, and billing platforms (e.g., Salesforce, Oracle Fusion, Net Suite, Stripe, Metronome).
• Exceptional communication skills, capable of cross‑functional collaboration and efficient resolution of customer issues.
• High detail orientation and a data‑driven mindset, skilled in analyzing complex billing scenarios and driving continuous process enhancements.
• A strong understanding of month‑end close, reconciliations, and SOX compliance frameworks.
• Demonstrated success driving automation initiatives and system implementations across the OTC cycle.
• Strong…