AI Deployment Manager - Pilots - San Francisco

About the Role The AI Deployment Manager (ADM) - Pilots is a customer-facing role responsible for leading structured, time-bound enterprise AI pilots from initial scoping through final executive readout. This role is focused on helping customers evaluate OpenAI’s products in real-world contexts, identify high-value use cases, and generate clear, decision-ready signals tied to business value. You will design and lead pilot engagements that drive activation, sustained usage, and measurable impact across ChatGPT Enterprise, Codex, and adjacent workflows. This includes partnering with customer stakeholders to define success criteria, guiding users from experimentation to real adoption, and translating pilot outcomes into clear recommendations that support expansion or purchase decisions. This role requires strong judgment, the ability to operate in ambiguity, and a consistent focus on connecting technical capabilities to business outcomes. You will regularly engage both executive stakeholders and working teams, adapting your approach to meet customers where they are and move them forward. In this role, you will: - Own the design and execution of enterprise AI pilots, including scoping, cohort definition, and success criteria aligned to a clear commercial decision. - Identify and prioritize a small set of high-impact use cases that can generate credible signal within a 30–45 day pilot. - Drive activation and sustained engagement across pilot cohorts through targeted enablement, office hours, and workflow-level coaching. - Monitor pilot performance and adapt in real time, diagnosing gaps in engagement, use case traction, or stakeholder alignment. - Translate pilot signals into clear, executive-ready recommendations, including whether and how the customer should expand. - Navigate customer constraints such as security, data access, and competing tools while maintaining pilot momentum. - Partner closely with ADs, SEs, and customer stakeholders to align on scope, risks, and

Department: Go To Market; Team: Technical Success