Head of Deal Strategy

OpenaiOpenai·Remote(San Francisco)
Other

WFA Digital Insight

The demand for skilled deal strategists has surged 25% in the past year, driven by the growing need for businesses to leverage AI in their operations. Openai, a pioneer in AI research and deployment, is seeking a Head of Deal Strategy to lead the development of world-class commercial proposals. With the remote job market booming, professionals with expertise in deal strategy, sales, and AI are in high demand. According to recent statistics, companies that effectively utilize AI in their sales processes see a 15% increase in revenue. As a leader in the field, Openai offers a unique opportunity to work at the forefront of AI innovation. Before applying, candidates should be aware of the company's commitment to safety and human-centered AI development, as well as its emphasis on collaboration and cross-functional teamwork.

Job Description

About the Role

The Head of Deal Strategy is a critical role at Openai, responsible for building and leading the team that creates world-class commercial proposals at scale. As AI becomes increasingly vital to business operations, the ability to translate complex products and commercial structures into compelling customer narratives is a strategic advantage. 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 role entails developing executive-ready proposals, building standardized ROI frameworks, supporting customer-facing conversations, and creating AI-native tools that enable consistent, high-quality deal support across the business. The Head of Deal Strategy will partner closely with teams across sales, pricing, deal desk, strategy, revops, and finance to develop a scalable proposal engine that helps Openai move faster, improve proposal quality, and win more effectively.

The ideal candidate will have experience in deal desk, deal strategy, strategic sales, or related functions, with a track record of building scalable processes, playbooks, and teams that improve deal execution across large organizations. They will also have strong communication and storytelling skills, with the ability to translate complex commercial concepts into compelling customer narratives.

What You Will 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.

What We Are Looking For

  • 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.

Nice to Have

  • Experience working in the AI or technology industry.
  • Knowledge of sales and marketing automation tools.
  • Certification in sales or marketing, such as a CRM or HubSpot certification.
  • Experience with data analysis and visualization tools, such as Tableau or Power BI.

Benefits and Perks

  • Competitive salary and benefits package.
  • Opportunity to work with a cutting-edge AI technology company.
  • Collaborative and dynamic work environment.
  • Professional development and growth opportunities.
  • Flexible remote work arrangements.
  • Access to the latest tools and technologies.
  • Comprehensive health and wellness package.
  • Generous PTO and holiday policy.

How to Stand Out

  • Tip: Highlight your experience with AI-powered sales tools and workflows in your application, as this is a key area of focus for the company.
  • Develop a strong understanding of the company's products and services, including its AI-powered solutions, to demonstrate your knowledge and enthusiasm for the role.
  • Create a portfolio of your work, including examples of successful sales strategies and proposals you've developed, to showcase your skills and experience.
  • Prepare to discuss your experience with cross-functional teamwork and collaboration, as this is a critical aspect of the Head of Deal Strategy role.
  • Research the company's culture and values, and be prepared to discuss how your own values and approach to work align with those of the company.
  • Consider seeking out additional training or certification in AI-powered sales tools and workflows to enhance your skills and competitiveness for the role.
  • Be prepared to provide specific examples of your experience with financial and analytical rigor, including building ROI models and executive-ready materials.

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