Head of Deal Strategy

OpenAI is seeking a Head of Deal Strategy to build and lead the team responsible for creating world-class commercial proposals at scale.

The base pay offered is $347K – $385K, with generous equity, performance-related bonuses, and the following benefits:

• 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
• 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

About the Role

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.

Responsibilities

• 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

Requirements

• 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