Deal Desk Sr. Lead

About the Team

OpenAI Finance ensures the company is commercially structured to support rapid growth while protecting long-term financial integrity. Within Finance, the Deal Desk function serves as the commercial backbone of enterprise sales—partnering across Sales, Legal, Revenue Operations, and Finance to enable high-quality, compliant, and scalable deal execution.

The Deal Desk team owns the commercial governance of customer transactions. We provide expert guidance on deal structure, pricing, discounting, and contractual economics while ensuring alignment with revenue recognition, policy, legal, and risk standards. Acting as a strategic partner to Sales, we help maximize deal quality, speed, and predictability while maintaining operational discipline at scale.

This team continuously improves how the company sells—driving standardization, strengthening controls, and building systems and workflows that allow OpenAI to grow efficiently across products, customer segments, and geographies.

About the Role

We are hiring a Deal Desk Senior Lead to build and scale a high-impact commercial execution function. This role will serve as a senior commercial deal leader, responsible for establishing best-in-class deal governance, enabling sales velocity, and ensuring that complex, high-value transactions are executed with speed, accuracy, and financial rigor.

This leader will oversee end-to-end Deal Desk operations, including deal structuring, approvals, contracting workflows, enabling GTM initiatives, and quote-to-cash alignment . You will partner closely with Sales, Revenue Operations, Billing, Legal, and Finance to create a globally consistent, highly scalable operating model for how OpenAI transacts with customers.

This is a highly visible role that sits at the intersection of revenue growth, financial controls, and customer experience.

In this role, you will:

• Serve as a trusted commercial advisor to Sales and cross-functional partners on complex, high-value deals, ensuring alignment with pricing strategy, revenue recognition, and company policies.

• Lead the governance of deal structure, discounting, non-standard terms, and approvals to balance growth, risk, and profitability.

• Enable sales teams to move faster by providing clear frameworks, guidance, and escalation paths for deal strategy and execution.

• Design and scale Deal Desk processes, tools, and operating rhythms that support high-volume, high-complexity enterprise selling.

• Ensure tight integration across quote-to-cash, including CPQ, contracting, billing, and revenue workflows.

• Drive continuous improvement through data, automation, and standardization while maintaining flexibility for strategic deals.

You might thrive in this role if you have:

• 6+ years of experience in Enterprise SaaS, Cloud, Ads or B2B environments across Deal Desk, Sales Operations, Finance Operations, or Order-to-Cash.

• Deep expertise in structuring and executing complex, multi-product, multi-term, or global enterprise transactions.

• Strong understanding of quote-to-cash, revenue recognition, and commercial risk management.

• Experience operating within enterprise systems such as Salesforce, CPQ, NetSuite, Stripe, Ironclad, or similar platforms.

• Exceptional communication and stakeholder management skills, with the ability to influence senior Sales, Finance, and Legal leaders.

• Accounting, audit, or finance background is appreciated.

About OpenAI

OpenAI is an AI research and deployment company dedicated to ensuring that general-purpose artificial intelligence benefits all of humanity. We push the boundaries of the capabilities of AI systems and seek to safely deploy them to the world through our products. AI is an extremely powerful tool that must be created with safety and human needs at its core, and to achieve our mission, we must encompass and value the many different perspectives, voices, and experiences that form the full spectrum of humanity. 

We are an equal opportunity employer, and we do not discriminate on the basis of race, religion, color, national origin, sex, sexual orientation, age, veteran status, disability, genetic information, or other applicable legally protected characteristic.

For additional information, please see OpenAI’s Affirmative Action and Equal Employment Opportunity Policy Statement.

Background checks for applicants will be administered in accordance with applicable law, and qualified applicants with arrest or conviction records will be considered for employment consistent with those laws, including the San Francisco Fair Chance Ordinance, the Los Angeles County Fair Chance Ordinance for Employers, and the California Fair Chance Act, for US-based candidates. For unincorporated Los Angeles County workers: we reasonably believe that criminal history may have a direct, adverse and negative relationship with the following job duties, potentially resulting in the withdrawal of a conditional offer of employment: protect computer hardware entrusted to you from theft, loss or damage; return all computer hardware in your possession (including the data contained therein) upon termination of employment or end of assignment; and maintain the confidentiality of proprietary, confidential, and non-public information. In addition, job duties require access to secure and protected information technology systems and related data security obligations.

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