Strategic Deals & Commercial Architecture Lead

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 behind it. They develop a clear point of view, recommend pragmatic paths forward, and align senior cross-functional stakeholders without formal authority. This role is based in San Francisco, CA. We use a hybrid work model of three days in the office per week and offer relocation assistance to new employees. IN THIS ROLE, YOU WILL: - Serve as the senior Deal Desk authority and commercial architect for complex, precedent-setting enterprise transactions, shaping deal structure, economics, terms, and approval strategy - Lead cross-functional deal strategy and governance, synthesizing input from Sales, Legal, Finance, Product, and operations to recommend clear, executable paths forward - Establish decision frameworks, guardrails, exception principles, and escalation paths that accelerate sound commercial decisions and protect financial and operational integrity - Translate novel commercial requirements into scalable quote-to-cash workflows and systems capabilities, identifying recurring friction and driving automation and process improvement - Assess the end-to-end implications of proposed deal structures across contracting, billing, revenue recognition, provisioning, reporting, controls, auditability, and customer experience - Convert deal precedent and recurring patterns into approval matrices, operating policies, playbooks, and enablement that improve organizational leverage and consistency WE’RE SEEKING SOMEONE WITH: - Typically 7+ years of individual-contributor experience in Deal Desk, commercial strategy, commercial operations, pricing and monetization, or a related enterprise SaaS function - Deep expertise structuring complex, non-standard enterprise transactions and evaluating tradeoffs among customer value, business velocity, economics, and risk - Strong command of quote-to-cash processes and the downstream operational and financial impacts of contracting, billing, and revenue recognition decisions - Exceptional judgment in ambiguity, with the ability to form a point of view, recommend a path forward, and influence senior stakeholders without formal authority - Hands-on experience with enterprise commercial systems such as Salesforce, CPQ, CLM, billing, and order-management platforms, including translating commercial policy into scalable system requirements PREFERRED QUALIFICATIONS - Experience with enterprise cloud business models and commercial constructs, including usage-based, committed-spend, and hybrid pricing models. - Experience supporting new products or monetization motions with complex contracting, provisioning, billing, or accounting dependencies. - Experience leading cross-functional policy, operating-model, or systems transformations that improved deal velocity, decision quality, or control effectiveness. YOU MIGHT THRIVE IN THIS ROLE IF YOU: - View Deal Desk as a strategic commercial capability and enjoy developing a point of view on complex, high-stakes decisions. - Br