Head of Deal Strategy

TL;DR

Head of Deal Strategy: Building and leading a deal support function that creates world-class commercial proposals at scale with an accent on scalable proposal mechanisms, ROI frameworks, and executive-ready deal narratives. Focus on designing an AI-native proposal engine (copilots, automated briefs, and guided workflows) and improving win rates through feedback loops across Sales, Pricing, Deal Desk, Finance, Legal, and RevOps.

Location: San Francisco

Salary: $347K–$385K + Offers Equity

Company

OpenAI is an AI research and deployment company building and safely deploying general-purpose AI.

What you will do

• Establish scalable deal support mechanisms, including proposal templates, negotiation playbooks, deal clinics, office hours, and structured intake processes.
• Build and maintain standardized ROI frameworks, calculators, and value narratives for consistent use across the field.
• Advise account teams on deal strategy for strategic opportunities, including executive narratives, competitive positioning, and ROI arguments.
• Develop customer-facing and CFO-ready proposals for complex, high-value, or first-of-kind deals.
• Convert bespoke proposal work into reusable assets to improve speed, consistency, and seller productivity.
• Create AI-native deal strategy capabilities using proposal copilots, automated deal briefs, knowledge retrieval, guided workflows, and self-service resources.

Requirements

• 12+ years of experience in deal desk, deal strategy, strategic sales, or related functions.
• Proven ability to build 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 to translate complex commercial concepts into compelling customer narratives.
• Financial and analytical rigor, including experience building ROI models and business cases.
• Experience leading cross-functional initiatives across Sales, Finance, Product, Legal, and Operations.

Culture & Benefits

• Compensation range of $347K–$385K plus offers equity.
• Opportunity to build AI-native tools that scale deal expertise and improve proposal quality.
• Cross-functional collaboration across Sales, Pricing, Deal Desk, Finance, Legal, RevOps, Enablement, and Strategy.