Deal Desk Sr. Lead

OpenAI • San Francisco, CA

1d

About The Position

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.
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.

Requirements

• 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.

Nice To Haves

• Accounting, audit, or finance background is appreciated.

Responsibilities

• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed
• Number of Employees: 5,001-10,000 employees