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 next steps.
• Capture patterns across pilots and turn them into repeatable playbooks that improve qualification, execution, and outcomes.

You’ll thrive in this role if you

• Have 8+ years of experience in enterprise consulting, customer success, program management, solutions engineering, or a similar customer-facing role, engaging executive and senior technical audiences.
• Have led structured pilots, POCs, or adoption programs tied to a clear business or commercial decision.
• Possess exceptional presentation and communication skills, particularly when conveying technical concepts and pilot outcomes clearly to executive stakeholders.
• Have experience driving product adoption and change management within large organizations, moving users from initial experimentation to sustained usage.
• Bring enough technical fluency to reason about data access, integrations, and common deployment constraints, and can connect technical capabilities to concrete business outcomes.
• Are comfortable operating in fast-paced, ambiguous environments, making tradeoffs in real time while maintaining clarity and momentum.
• Bring a high ownership mindset and collaborative approach, proactively driving outcomes across sales, technical, and customer stakeholders.
• Are personally committed to the responsible and ethical deployment of AI.