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OpenAI

Head of Deal Strategy

Lead the Deal Strategy team to build scalable proposal processes, ROI frameworks, and AI-native tools that help account teams win complex, high-value deals. Partner with Sales, Pricing, Finance, Legal, and Product to drive consistent, high-quality commercial outcomes.

347k – 385kSan Francisco, CARevenue OperationsHybrid12+ YOE
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About the role

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.

Skills

Deal StrategyDeal DeskRoi ModelingBusiness Case DevelopmentProposal DevelopmentNegotiation PlaybooksCross-Functional CollaborationSales EnablementFinancial AnalysisAi Workflow Automation

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