# Head of Deal Strategy
**Company:** [OpenAI](https://hotfix.jobs/companies/openai)
**Location:** San Francisco, CA
**Salary:** $347K-$385K
**Experience:** 12+ years
**Skills:** Deal Strategy, Deal Desk, Roi Modeling, Business Case Development, Proposal Development, Negotiation Playbooks, Cross-Functional Collaboration, Sales Enablement, Financial Analysis, Ai Workflow Automation
**Posted:** 2026-06-22
> 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.
## Job Description
## 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.
**Apply:** https://hotfix.jobs/jobs/head-of-deal-strategy-at-openai-d557f2ac-0e5f-40f6-ad9d-56e9eac3043f
**Canonical:** https://hotfix.jobs/jobs/head-of-deal-strategy-at-openai-d557f2ac-0e5f-40f6-ad9d-56e9eac3043f