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, ROI arguments, and proposal approaches for strategic opportunities.
• Partner closely with Pricing, Deal Desk, Finance Engineering, Product, Legal, Revenue Operations, Enablement, and Strategy to ensure proposals reflect current products, campaigns, and commercial guidance.
• Develop customer-facing and CFO-ready proposals for complex, high-value, or first-of-kind deals.
• Join customer conversations to present proposal recommendations, business cases, and the logic behind commercial structures when senior support is needed.
• Convert bespoke proposal work into reusable assets that improve speed, consistency, and seller productivity.
• Create an AI-native deal strategy capability through proposal copilots, automated deal briefs, knowledge retrieval systems, guided workflows, and self-service resources.
• Create feedback loops to identify where deals deviate from standard approaches and surface insights that improve products, policies, and field motions over time.

You Might Thrive in This Role If You Have

• 12+ years of experience in deal desk, deal strategy, strategic sales, or related functions.
• A track record of building scalable processes, playbooks, and teams that improve deal execution across large organizations.
• Experience advising field teams and executive stakeholders on complex, high-value, or first-of-kind deals.
• Strong communication and storytelling skills, with the ability to translate complex commercial concepts into compelling customer narratives.
• Financial and analytical rigor, including experience building ROI models, business cases, and executive-ready materials.
• Experience leading cross-functional initiatives across Sales, Finance, Product, Legal, and Operations teams.
• Familiarity with using AI to improve workflows, scale expertise, and increase team productivity.