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Deal Desk Senior Lead

United States, San Francisco 162000.00 - 180000.00 USD / Year · Job Posted February 21, 2026
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Job Description

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.

Job Responsibility

  • 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

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
  • Accounting, audit, or finance background is appreciated

Nice to have

Accounting, audit, or finance background

What we offer

  • Medical, dental, and vision insurance for you and your family, with employer contributions to Health Savings Accounts
  • Pre-tax accounts for Health FSA, Dependent Care FSA, and commuter expenses (parking and transit)
  • 401(k) retirement plan with employer match
  • Paid parental leave (up to 24 weeks for birth parents and 20 weeks for non-birthing parents), plus paid medical and caregiver leave (up to 8 weeks)
  • Paid time off: flexible PTO for exempt employees and up to 15 days annually for non-exempt employees
  • 13+ paid company holidays, and multiple paid coordinated company office closures throughout the year for focus and recharge, plus paid sick or safe time (1 hour per 30 hours worked, or more, as required by applicable state or local law)
  • Mental health and wellness support
  • Employer-paid basic life and disability coverage
  • Annual learning and development stipend to fuel your professional growth
  • Daily meals in our offices, and meal delivery credits as eligible
  • Relocation support for eligible employees
  • Additional taxable fringe benefits, such as charitable donation matching and wellness stipends

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