Billing Operations Lead in San Francisco

About the Team OpenAI’s Finance and Revenue Operations organization builds the commercial infrastructure that enables the business to scale with speed, discipline, and financial integrity. Deal Desk operates as the commercial strategy and governance function at the intersection of Sales, Partnerships, Legal, Technical Revenue, Finance, Order Management, Billing Operations, Product, and GTM Systems. We architect complex enterprise transactions, turn ambiguity into executable decisions, and create the guardrails that let the business move quickly with operational and financial discipline. As OpenAI’s enterprise business grows in scale and complexity, Deal Desk defines how novel commercial motions become durable operating capabilities. We convert precedent-setting deal decisions into repeatable policy, controls, workflows, and systems requirements. About the Role We are hiring a Strategic Deals & Commercial Architecture Lead to lead the structuring and governance of OpenAI’s most complex enterprise transactions. This is a senior individual-contributor leadership role for someone with exceptional enterprise deal judgment, operational rigor, and a builder mindset. You will serve as the commercial architect for high-stakes opportunities, translating ambiguous requirements into coherent deal structures, approval strategies, and executable quote-to-cash plans. Your work will shape more than individual transactions. You will establish decision principles and precedent, clarify tradeoffs, and turn recurring patterns into scalable guidance, controls, systems requirements, and enablement. You will own the commercial decision and governance layer that helps strategic opportunities move decisively while managing downstream risk across contracting, billing, revenue recognition, provisioning, reporting, controls, auditability, and customer experience. The right candidate can move seamlessly between advising on a single high-value transaction and improving the operating model be

About the Team OpenAI Finance ensures the organization is positioned for long-term success as we pursue our mission. The Revenue team plays a critical role in enabling OpenAI to scale commercial offerings by overseeing billing operations, deal desk, revenue systems, revenue accounting, and controllership. We work cross-functionally with Product, Engineering, Go-To-Market, Tax, Legal, and Technical Accounting to support new monetization strategies, improve operational efficiency, and maintain financial integrity as the business grows. About the Role This senior leader will own key elements of Ads revenue accounting from technical assessment through operational execution. The role will guide accounting for products, pricing, contracts, incentives, credits, refunds, makegoods, international expansion, and new go-to-market motions. It will establish governance and translate approved accounting positions into launch, billing, data, close, reconciliation, and control requirements. Success requires deep technical revenue expertise, strong business partnership, and the ability to build durable 0-to-1 processes in a fast-changing environment. Advertising is a critical and growing monetization vector for OpenAI, and this role will help shape the financial foundations that enable Ads to scale responsibly and transparently. 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. In this role, you will: Lead technical accounting assessments for Ads products and commercial arrangements, including performance obligations, variable consideration, allocation, principal-versus-agent, collectibility, contract modifications, refunds, incentives, credits, makegoods, and revenue presentation. Own and continuously evolve Ads revenue accounting policies and operating guidance as product behavior, pricing, contracting, incentive programs, and billing models change. Establish governance for new pro

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. About the Role We are seeking a Senior Manager to build and scale Order to Cash across OpenAI’s API and ChatGPT businesses, cloud marketplaces, and strategic partnership channels. This role will own end-to-end Order Management and Billing operations across API and ChatGPT while leading OTC readiness and execution for AWS Marketplace, Google Cloud Marketplace, Oracle Cloud Marketplace, GovCloud, and future partner channels. The role will also own the end-to-end Order Management and Billing close, setting the close calendar, readiness standards, review and sign-off expectations, while leading the team responsible for execution. You will oversee the Order Management and Billing lifecycle across API, ChatGPT, marketplace, and partner transactions, spanning commercial readiness, order intake, provisioning, usage and transaction data, pricing validation, invoicing, credits, settlements, and product and partner reporting. Your work will ensure transactions are accurate, timely, complete, and supported by audit-ready controls. This is a leadership role that combines strategic ownership, cross-functional leadership, and hands-on operational execution. You will define the target operating model, lead first-of-kind launches, shape product and systems roadmaps, and oversee the resolution of complex contract modifications, non-standard pricing, usage disputes, reconciliation breaks, settlement variances, and customer- or partner-impacting escalations. You will collaborate with teams across Finance, GTM, Product, Engineering, Legal, Tax, Reven

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. About the Role We are looking for a senior, hands-on operator to own Order Management and Billing execution across OpenAI’s cloud marketplace and partner ecosystem, including platforms such as AWS, GCP, Oracle Cloud, GovCloud, and future channels. This senior individual contributor role will translate partner requirements into scalable workflows and ensure launch readiness, accurate billing, and reliable daily execution. As a senior individual contributor within the Cloud Marketplaces team, you will own the end-to-end order-to-invoice lifecycle for your assigned portfolio. You will ensure that private offers, commercial terms, provisioning, pricing, usage, billing data, credits, settlements, and partner-specific reporting flow through our systems accurately, on time, and with audit-ready controls. You will implement and continuously improve the common cloud marketplace operating model, lead cross-functional execution for your assigned portfolio, and surface risks, requirements, and improvement opportunities. You will partner across Revenue Systems, Product, Engineering, GTM, Finance, Partner Operations, and external marketplace stakeholders. This role is critical to building the operational backbone for OpenAI’s expansion across cloud marketplaces and government-cloud channels. You will combine deep operational judgment with process and control execution, automation, clear communication, and hands-on problem solving to improve billing reliability, partner experience, customer outcomes, and financial integrity at scale. This role

About the Team The Ads Support Delivery team is responsible for helping successfully operate and grow on our Ads product. This includes technical guidance, troubleshooting complex delivery and monetization issues, and partnering closely with Product, Engineering, Trust & Safety and Go-To-Market teams to resolve customer-impacting problems and improve the platform over time. The team’s mission is to deliver a high-quality customer experience at scale by combining strong human support with automation, self-service, and AI-enabled workflows, while maintaining high operational rigor. About the Role: As a Support Delivery Lead for Ads, you will lead a team responsible for end-to-end support delivery across the ads ecosystem, including campaign setup, delivery, billing, measurement, and policy navigation. You will set the operational bar for quality, responsiveness, and consistency; coach and grow the team; and translate support signals into actionable improvements with Engineering, Product, and Go-To-Market partners. 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. In this role, you will: Lead and support a team of Ads support engineers, ensuring they have the tools, clarity, and coaching needed to operate at a high bar in a technically complex domain. Set clear expectations and operating standards, run recurring performance reviews, and build development plans that grow both technical depth (ad tech fluency) and customer-facing excellence. Design and continuously improve support coverage for ad buyers, ensuring the team can diagnose delivery issues and monetization and integration issues with equal rigor. Act as the bridge between Support Delivery, Engineering, Product, and Go-To-Market teams. Drive alignment on priorities, escalation paths, launch readiness, tooling improvements and mechanisms to reduce repeated customer pain points. Partner with engineering teams

About the Team OpenAI’s Finance and Revenue Operations organization builds the commercial infrastructure that enables the business to scale with speed, discipline, and financial integrity. Within Revenue Operations, Deal Desk partners closely with Sales, Partnerships, Product, Engineering, Legal, Technical Revenue, Finance, Billing, Order Management, and GTM Systems to turn complex commercial opportunities into executable, scalable transactions. About the Role We are hiring a Strategic Deals & Commercial Architecture Lead — Marketplaces & Partnerships to own the commercial architecture, execution, and governance layer for marketplace-enabled and partner-led transactions. This senior individual-contributor role is for someone who combines enterprise deal judgment, marketplace fluency, analytical rigor, and a builder mindset. You will take shaped opportunities from intake through approval and launch readiness, translating first-of-kind structures into clear economics, executable terms, quote-to-cash requirements, controls, and operating mechanisms. You will partner closely with teams that own business development and partner relationships; this role does not own partner sourcing, pipeline generation, or sales closing. You will support the commercial requirements for onboarding and integration without owning technical delivery. Success is measured both by the decisions and deals you enable and by the durable policies, systems, and controls you leave behind. This role is based in San Francisco, CA. We use a hybrid work model of three office days per week and offer relocation assistance. In This Role, You Will Lead the commercial architecture and execution of complex marketplace-enabled and partner-led enterprise transactions from intake through approval, contracting, launch readiness, and operational handoff. Structure private offers, pricing, fees, incentives, commitments, revenue share, credits, renewals, amendments, and other non-standard or multi-party terms

ABOUT BASETEN Baseten powers mission-critical inference for the world's most dynamic AI companies, like Cursor, Notion, OpenEvidence, Abridge, Clay, Gamma and Writer. By uniting applied AI research, flexible infrastructure, and seamless developer tooling, we enable companies operating at the frontier of AI to bring cutting-edge models into production. We're growing quickly and recently raised our $1.5B Series F , led by Altimeter Capital, Conviction Partners, and Spark Capital. Join us and help build the platform engineers turn to to ship AI products. THE ROLE We're looking for a Finance Systems Lead to own and evolve the systems that support Baseten's finance operations, including ERP, planning tools, and the broader finance and adjacent systems stack, spanning HRIS/payroll, CPQ, and commissions, as we implement, integrate, and automate across them. As Baseten scales, so does the number of systems finance depends on and touches, from the ERP to planning to compensation and quote to cash tooling. This role exists to bring a dedicated owner to that stack, someone who can lead implementations (partnering with contractors or vendor CSMs for hands-on technical configuration where needed), keep systems integrated and clean as we grow, and find automation opportunities that save the team time. This is a highly cross-functional role. You will partner with Accounting, FP&A, People, Sales and Revenue Operations, Legal, and IT to understand how each team uses its systems, and design integrations and workflows that serve the business without creating more manual work. RESPONSIBILITIES Core Finance Systems Own finance systems strategy, configuration, and roadmap, partnering with contractors or vendor CSMs on hands-on technical configuration as needed Lead the implementation and ongoing administration of our finance systems and tools Own finance system integrations end to end, ensuring clean data flow between ERP, planning, billing, and other systems, partnering with contrac

About the Team The DeployCo Deal Desk helps turn customer deployment opportunities into clear, executable professional-services engagements. We partner across Deployment, Sales, Legal, Finance, Technical Revenue, and Operations to ensure every deal has a well-defined scope, pricing aligned to approved guardrails, complete approvals, and a clean handoff to delivery. The team sits at the intersection of commercial execution and delivery readiness. We make complex services deals easier to buy—and easier to deliver—while strengthening the templates and workflows that help DeployCo scale. About the Role We are hiring a hands-on Professional Services Commercial Lead to own the end-to-end deal desk workflow for assigned DeployCo professional-services engagements. You will personally draft and revise statements of work (SOWs), validate pricing and deal inputs, coordinate cross-functional reviews and approvals, and ensure commitments are clear, deliverable, and ready to execute. The differentiator in this role is drafting expertise: you have written SOWs, not simply routed them. You can turn technical and delivery inputs into precise scope, deliverables, milestones, assumptions, dependencies, acceptance criteria, fees, and change controls—then keep the deal moving. This is an individual-contributor role for an experienced contract manager, deal desk professional, or professional-services commercial operator who combines strong writing and commercial judgment with disciplined execution. What You’ll Do Own assigned DeployCo deals from intake through approval, signature, and operational handoff. Draft and revise SOWs, work orders, and change orders using approved templates and playbooks; partner with Legal on non-standard contractual terms and redlines. Validate rate cards, fees, hours and resourcing inputs, discounts, margin inputs, billing milestones, and key deal data against approved inputs and guardrails; reconcile the SOW to the quote and route exceptions with a clear rec

About the Team The DeployCo Deal Desk helps turn customer deployment opportunities into clear, executable professional-services engagements. We partner across Deployment, Sales, Legal, Finance, Technical Revenue, and Operations to ensure every deal has a well-defined scope, pricing aligned to approved guardrails, complete approvals, and a clean handoff to delivery. The team sits at the intersection of commercial execution and delivery readiness. We make complex services deals easier to buy—and easier to deliver—while strengthening the templates and workflows that help DeployCo scale. About the Role We are hiring a hands-on Professional Services Commercial Lead to own the end-to-end deal desk workflow for assigned DeployCo professional-services engagements. You will personally draft and revise statements of work (SOWs), validate pricing and deal inputs, coordinate cross-functional reviews and approvals, and ensure commitments are clear, deliverable, and ready to execute. The differentiator in this role is drafting expertise: you have written SOWs, not simply routed them. You can turn technical and delivery inputs into precise scope, deliverables, milestones, assumptions, dependencies, acceptance criteria, fees, and change controls—then keep the deal moving. This is an individual-contributor role for an experienced contract manager, deal desk professional, or professional-services commercial operator who combines strong writing and commercial judgment with disciplined execution. In this role, you will: Own assigned DeployCo deals from intake through approval, signature, and operational handoff. Draft and revise SOWs, work orders, and change orders using approved templates and playbooks; partner with Legal on non-standard contractual terms and redlines. Validate rate cards, fees, hours and resourcing inputs, discounts, margin inputs, billing milestones, and key deal data against approved inputs and guardrails; reconcile the SOW to the quote and route exceptions with a

About the Team We are a small and fast-moving partnerships team that shapes and executes OpenAI’s most important collaborations. Your mission is to define and lead the strategy, roadmap, operating model, and growth of OpenAI’s B2B marketplace. You will build the scalable foundation through which customers discover, evaluate, adopt, and manage trusted third-party solutions built on and with OpenAI’s models. About the Role You are a senior marketplace and ecosystem leader with strong judgment, high ownership, and a track record of building scaled B2B platforms. You are comfortable moving between product design, commercial strategy, ecosystem development, and operations, and you can create clarity where there is no playbook. You bring the credibility to align senior internal and external stakeholders while moving quickly and executing at a high bar. Key Responsibilities Define the vision, strategy, roadmap, and success metrics for OpenAI’s marketplace. Own marketplace business performance across partner supply, customer demand, adoption, transaction volume, partner success, solution quality, and customer trust. Partner closely with product and engineering to shape discovery, listing, evaluation, procurement, billing, deployment, identity, governance, security, and measurement capabilities. Build a high-quality ecosystem of ISVs, developers, service providers, and other third-party solution partners. Design marketplace commercial models, policies, incentives, and partner economics with finance, legal, security, policy, and operations. Create scalable go-to-market motions across sales, co-sell, private offers, marketing, and customer success. Establish standards for solution quality, safety, compliance, performance, and lifecycle management. Build and lead the marketplace team and operating cadence, aligning cross-functional owners against clear priorities and outcomes. Qualifications 15+ years of experience in marketplaces, platforms, ecosystems, product, partnerships,

Why Join The Drata Team? The best way to understand the Driver’s Mindset is to see it in action. We’re an award-winning, mission-driven team of 600+ people worldwide , united by a culture that values trust, speed, and continuous growth. Hear the Voice of the Team : Explore our "Life at Drata" page for employee testimonials on our collaborative and the growth opportunities available. Connect with Us on Socials: LinkedIn - follow us for company updates, employee stories, and career news. Job Summary: The Staff Software Engineer, Monetization Platform serves as a technical leader with a primary focus on the systems that turn product usage, subscriptions, credits, commitments, and contracts into accurate customer outcomes and clean financial operations. This person will architect and evolve the core billing domain for Drata: usage event ingestion, billable metrics, pricing and packaging, invoice generation, entitlement enforcement, and the integrations that connect engineering to Accounting, Finance, RevOps, Salesforce, CPQ, and ERP systems like NetSuite. They should be equally comfortable designing event-driven systems, shaping commercial flexibility with business stakeholders, and building operationally trustworthy software where correctness, audit-ability, and scale matter. Modern billing is no longer just “charge a credit card once a month” — it is a real-time product control plane that must support evolving pricing models without turning the codebase into a fragile mess. What you’ll do: Partner with Product, Finance, Accounting, RevOps, and Engineering leadership to shape Drata’s long-term billing architecture and commercial flexibility across self-serve and enterprise motions. Design the primitives of a modern billing platform: usage events, billable metrics, products, rate cards, contracts, credits, subscriptions, overages, and invoice workflows. Architect a system that can accurately meter product usage at scale, transform raw events into billable quantities, an

ABOUT BASETEN Baseten powers mission-critical inference for the world's most dynamic AI companies, like Cursor, Notion, OpenEvidence, Abridge, Clay, Gamma and Writer. By uniting applied AI research, flexible infrastructure, and seamless developer tooling, we enable companies operating at the frontier of AI to bring cutting-edge models into production. We're growing quickly and recently raised our $1.5B Series F , led by Altimeter Capital, Conviction Partners, and Spark Capital. Join us and help build the platform engineers turn to to ship AI products. THE ROLE: As a Software Engineer at Baseten, you will own one of the most critical surfaces of our business: pricing, billing, and revenue infrastructure. As we launch more and more products— billing is no longer just operational plumbing. It is a strategic lever for growth. This role will establish clear ownership of billing as a function and create leverage for Finance, Sales, and GTM teams while maintaining a seamless customer experience. RESPONSIBILITIES: Own Baseten’s end-to-end billing and revenue infrastructure, including pricing, invoicing, metering, and reporting foundations. Build and evolve our billing platform and integrations (including Orb), ensuring correctness, auditability, and a high-trust experience for customers and internal teams. Partner closely with Finance, Sales, GTM, and Forward Deployed Engineering to turn real-world workflows into reliable internal tooling and automation (quoting, approvals, renewals, usage reconciliation, revenue reporting). Design systems that scale with new products, packaging, and go-to-market motions, making billing a strategic lever for growth. Drive reliability and operational excellence for revenue-critical workflows: monitoring, alerting, incident response, backfills, and clear runbooks. Lead from the front on high-impact projects: clarify requirements, propose crisp technical approaches, ship iteratively, and raise the bar on quality and velocity. Debug and resolve

About Sentry Software runs the world and the pace is faster than ever. Sentry helps developers fix errors and performance issues before users notice, so teams can spend less time firefighting and more time building. Trusted by 200,000+ organizations, Sentry is today’s application monitoring standard and our team is building its AI-native future. About the team The Billing team sits at the intersection of product, finance, and infrastructure. They're responsible for ensuring every observable event—errors, logs, traces, tokens—gets accurately measured, priced, and billed. Their work directly impacts company revenue and customer trust, requiring distributed systems expertise, attention to financial accuracy, and deep understanding of product usage patterns. The team works cross-functionally with product, engineering, BizOps, marketing, and sales to build systems that enable new products and pricing models. As an Engineering Manager, you’ll lead a team of engineers owning critical workflows such as checkout and invoicing, while also developing new features to help customers manage their spend growth. In this role, you’ll partner across the organization to ensure our customers redeem everything Sentry has to offer and budget for future expansion. In this role you will Strategic Planning & Roadmap: Define and drive the team's roadmap. Align team goals with organizational objectives and contribute to the overall platform strategy. Technical Guidance & Operational Excellence: Provide technical leadership and guidance on complex distributed systems and design. Ensure the team is proactively identifying areas for improvement. Cross-functional Collaboration: Partner closely with business and technical teams to translate business goals into actionable objectives and scalable solutions. Team Leadership & Development: Lead, mentor, and grow a team of talented engineers, including Staff-level engineers. Build a culture of technical excellence, collaboration, continuous

About the Team The Applied organization brings OpenAI’s most advanced technology to the world through products like ChatGPT and the APIs that power a growing ecosystem of developer and enterprise applications. Data Engineering builds and operates the trustworthy, secure, and reliable data systems that power decisions across OpenAI. About the Role We’re looking for a Data Engineering Manager to lead the Growth & Revenue data engineering team. This leader will own the data strategy and execution for the data subject areas spanning growth accounting across all product surfaces, product partnerships, checkout, billing, payments, revenue, and monetization, helping OpenAI understand how people adopt, engage with, and pay for our products. You will partner closely with several Data Science, Business, and Engineering partners to connect product behavior to trustworthy subscriber, payment, and revenue measurement. In this role, you will: Build, manage, and grow a high-performing, inclusive team across the Growth & Revenue data subject areas. Define the data strategy for all the data subject areas you own. Deliver durable, well-modeled data products that connect product behavior, subscription state, checkout events, payment outcomes, and revenue. Establish trusted metric definitions and data quality standards so product, growth, finance, and executive leaders can make fast, consistent decisions. Partner with Data Science and Product teams to support experimentation, causal measurement, funnel analysis, and scalable self-serve analytics. Partner with Finance and Financial Engineering to ensure analytical revenue views reconcile to financial truth and production billing systems. Raise operational excellence for critical pipelines, including reliability, observability, privacy, governance, and incident response. Set a clear roadmap, make principled tradeoffs, and communicate progress and risk across technical and business stakeholders. You might thrive in this role if yo

About The Team OpenAI Finance is responsible for ensuring the organization is set up for success in pursuit of its mission. The Technical Accounting team plays a crucial role in helping OpenAI navigate complex, judgmental, and rapidly evolving accounting matters with rigor and clarity. We aim to bring both technical excellence and strong business partnership to some of the most novel accounting questions in the industry. About The Role OpenAI seeks a Director, Technical Accounting, Revenue & Strategic Partnerships to set the technical revenue accounting strategy for the company's largest, most complex, and highest-risk commercial arrangements. This leader will personally assess novel fact patterns, establish and defend the accounting position, and shape deal structures before execution across enterprise contracts, strategic partnerships, API and consumption-based offerings, credits and incentives, revenue share, multi-party arrangements, and emerging product monetization models. This role will be the senior technical accounting partner to Revenue Accounting, Sales, Product, Legal, Tax, Strategic Finance, Business Development, Deal Desk, Billing, Financial Reporting, Internal Controls, and external auditors. The core mandate is technical judgment: independently synthesize the full contractual and economic substance, identify alternatives and second-order implications, resolve ambiguity under ASC 606 and related U.S. GAAP, and communicate a clear recommendation to executives and auditors. Operational know-how is essential to translate conclusions into billing, close, disclosures, systems, and controls, but process ownership is not the center of the role. In This Role, You Will Partner closely with Revenue Accounting, Sales, Product, Legal, Tax, Strategic Finance, Business Development, Deal Desk, Billing, Financial Reporting, and external auditors. Identify non-standard revenue arrangements early and evaluate them under ASC 606. Advise on thoughtful deal structurin