Head of Strategic Execution

OpenAI’s enterprise customers are making significant investments in AI, and adoption is accelerating. But meaningful AI transformation is not just a technology rollout, it reshapes how organizations operate, make decisions, and create value.

The AI Strategy & Adoption team partners with OpenAI’s most strategic enterprise customers to guide them through that transformation. We work directly with executive leaders to translate frontier AI capabilities into new operating models, workforce transformation, and measurable business outcomes.

Our mission is to help organizations move from AI experimentation to sustained enterprise capability, enabling them to continuously innovate and reinvent their business.

• We are seeking a senior leader with experience designing and facilitating high-impact executive journeys that turn complexity into clarity, alignment, and momentum.

• In this role, you will work alongside the Head of AI Strategy & Adoption to design and deliver the experience environments through which OpenAI engages enterprise leaders in AI transformation. This role will help shape how OpenAI partners with enterprise leadership teams to understand and act on the implications of frontier AI.

• You will architect the human interactions, workshops, and structured moments through which executive teams explore the implications of AI and align on a transformation roadmap. You will also help design the AI-native methods, tools, and digital layers that make these experiences more insightful, participatory, adaptive, and scalable.

• Your role is to ensure these engagements are strategically sound, experientially powerful, and increasingly powered by the capabilities OpenAI brings to market.

• Design and lead executive engagements, immersive sessions, workshops, and transformation experiences for OpenAI’s most strategic enterprise customers, using AI-native methods to improve preparation, personalization, participation, synthesis, and follow-through.

• Translate frontier AI capabilities into clear, compelling, and decision-ready experiences for senior leaders.

• Model AI-native ways of working for both customers and internal teams, demonstrating how frontier models can enhance strategic preparation, workshop design, live facilitation, synthesis, and action planning.

• Facilitate high-stakes conversations with executive leadership teams that help organizations move from ambiguity to alignment on vision, priorities, measures of success, and roadmaps. These engagements support commitment to execution and enable a formalized handoff to Strategic Execution.

• Partner with senior leaders to establish measures of success and initial accountability for transformation initiatives.

• Architect the end-to-end customer journey across key moments of the AI Strategy & Adoption motion, including LEAP and future engagement models.

• Define and evolve repeatable experience frameworks, formats, and standards that scale OpenAI’s enterprise transformation work while maintaining depth and quality.

• Partner closely with Executive Engagement and Strategic Execution leads to ensure strategic narrative, experiential design, and execution remain tightly integrated.

• Help shape the digital and application layer behind the motion, ensuring tools and platforms enhance executive understanding, participation, and follow-through.

• Help define and evolve OpenAI’s enterprise transformation methodology through insights generated from executive engagements.

• As this motion evolves, this role may also help build and mentor a small team responsible for scaling executive engagement experiences.

• Use AI fluently in your own work and see frontier models not just as content tools, but as design material for new kinds of executive experiences.

• Can imagine and prototype AI-powered experiences that go beyond traditional workshops and presentations.

• Are excited by the opportunity to combine facilitation craft, strategic judgment, and lightweight product or prototyping instincts to shape how these experiences are powered.

• Know how to use technology to deepen participation, accelerate synthesis, and create continuity before, during, and after executive engagements.

• Can engage credibly with CEOs, C-suite leaders, and senior operators as a strategic facilitator and guide.

• Bring strong judgment about how leaders absorb new ideas, build conviction, and commit to action together.

• Have strong instincts for experience design, narrative flow, moderation, and the human dynamics of transformation.

• Are able to translate complex technical capabilities into accessible and strategically meaningful executive conversations.

• Can build repeatable frameworks and high standards while adapting to the needs of each customer and context.

• Lead with presence, empathy, rigor, and thoughtful judgment in high-stakes environments.

We recognize that candidates bring diverse experiences and perspectives. If you’re excited about this role but your background doesn’t perfectly match every qualification, we encourage you to apply.

About OpenAI

OpenAI is an AI research and deployment company dedicated to ensuring that general-purpose artificial intelligence benefits all of humanity. We push the boundaries of the capabilities of AI systems and seek to safely deploy them to the world through our products. AI is an extremely powerful tool that must be created with safety and human needs at its core, and to achieve our mission, we must encompass and value the many different perspectives, voices, and experiences that form the full spectrum of humanity. 

We are an equal opportunity employer, and we do not discriminate on the basis of race, religion, color, national origin, sex, sexual orientation, age, veteran status, disability, genetic information, or other applicable legally protected characteristic.

For additional information, please see OpenAI’s Affirmative Action and Equal Employment Opportunity Policy Statement.

Background checks for applicants will be administered in accordance with applicable law, and qualified applicants with arrest or conviction records will be considered for employment consistent with those laws, including the San Francisco Fair Chance Ordinance, the Los Angeles County Fair Chance Ordinance for Employers, and the California Fair Chance Act, for US-based candidates. For unincorporated Los Angeles County workers: we reasonably believe that criminal history may have a direct, adverse and negative relationship with the following job duties, potentially resulting in the withdrawal of a conditional offer of employment: protect computer hardware entrusted to you from theft, loss or damage; return all computer hardware in your possession (including the data contained therein) upon termination of employment or end of assignment; and maintain the confidentiality of proprietary, confidential, and non-public information. In addition, job duties require access to secure and protected information technology systems and related data security obligations.

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