Head of Deal Strategy

About the Role OpenAI is seeking a Head of Deal Strategy to build and lead the team responsible for creating world-class commercial proposals at scale. As AI becomes increasingly critical to how organizations operate, the ability to translate complex products and commercial structures into compelling customer narratives is a strategic advantage. The Deal Strategy team will serve as an embedded partner to the field organization, helping account teams shape and communicate the right commercial path for strategic opportunities. The team will develop executive-ready proposals, build standardized ROI frameworks, support customer-facing conversations, and create AI-native tools that enable consistent, high-quality deal support across the business. This role partners closely with teams across sales, pricing, deal desk, strategy, revops & finance to develop a scalable proposal engine that helps OpenAI move faster, improve proposal quality, and win more effectively. What You'll Do - Establish scalable mechanisms for deal support, including proposal templates, negotiation playbooks, deal clinics, office hours, and structured intake processes. - Build and maintain standardized ROI frameworks, calculators, and value narratives that can be used consistently across the field. - Partner with account teams to advise on deal strategy, including executive narratives, competitive positioning, RO...