Head of Deal Strategy

Responsibilities

• Build and lead a team responsible for creating world-class commercial proposals and scalable deal strategy mechanisms.
• Establish scalable mechanisms for deal support, including proposal templates, negotiation playbooks, and structured intake processes.
• Build and maintain standardized ROI frameworks, calculators, and value narratives for use across the field.
• Partner with account teams to advise on deal strategy, executive narratives, and competitive positioning for strategic opportunities.
• Collaborate with Pricing, Deal Desk, Finance, Product, Legal, and Revenue Operations to ensure proposals reflect current commercial guidance.
• Develop customer-facing and CFO-ready proposals for complex, high-value, or first-of-kind deals.
• Create AI-native deal strategy capabilities, such as proposal copilots and automated deal briefs.

Requirements

• 12+ years of experience in deal desk, deal strategy, strategic sales, or related functions.
• Proven track record of building scalable processes, playbooks, and teams within large organizations.
• Experience advising field teams and executive stakeholders on complex, high-value deals.
• Strong storytelling and communication skills to translate complex commercial concepts into compelling narratives.
• High level of financial and analytical rigor, including experience building ROI models and business cases.
• Experience leading cross-functional initiatives across Sales, Finance, Product, Legal, and Operations.
• Familiarity with using AI to improve workflows and scale expertise.

Benefits

• Medical, dental, and vision insurance for you and your family.
• 401(k) retirement plan with employer match.
• Flexible PTO and paid parental leave.
• Annual learning and development stipend.
• Daily meals in our offices and meal delivery credits.
• Generous equity and performance-related bonuses.

About the Company

OpenAI is an AI research and deployment company dedicated to ensuring that general-purpose artificial intelligence benefits all of humanity. We push the boundaries of the capabilities of AI systems and seek to safely deploy them to the world through our products.