AI Deployment Manager - Pilots - San Francisco

Details

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 focuses 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.

Responsibilities

• 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 Account Directors, Solutions Engineers, 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.

Requirements

• 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.
• Experience leading structured pilots, POCs, or adoption programs tied to a clear business or commercial decision.
• Exceptional presentation and communication skills, particularly when conveying technical concepts and pilot outcomes to executive stakeholders.
• Experience driving product adoption and change management within large organizations, moving users from initial experimentation to sustained usage.
• Technical fluency sufficient to reason about data access, integrations, and common deployment constraints and to connect technical capabilities to concrete business outcomes.
• Comfort operating in fast-paced, ambiguous environments, making tradeoffs in real time while maintaining clarity and momentum.
• High ownership mindset and collaborative approach, proactively driving outcomes across sales, technical, and customer stakeholders.
• Commitment to the responsible and ethical deployment of AI.

About OpenAI

OpenAI is an AI research and deployment company dedicated to ensuring that general-purpose artificial intelligence benefits all of humanity. The company emphasizes safety and human needs in AI development and values diverse perspectives and experiences. OpenAI is an equal opportunity employer and provides information about affirmative action and applicant privacy policies. Background checks will be administered in accordance with applicable law.

Benefits

• Medical, dental, and vision insurance with employer contributions to Health Savings Accounts
• Pre-tax accounts for Health FSA, Dependent Care FSA, and commuter expenses
• 401(k) retirement plan with employer match
• Paid parental leave (up to 24 weeks for birth parents and 20 weeks for non-birthing parents), plus paid medical and caregiver leave (up to 8 weeks)
• Paid time off: flexible PTO for exempt employees and up to 15 days annually for non-exempt employees
• 13+ paid company holidays and multiple coordinated company office closures
• Mental health and wellness support
• Employer-paid basic life and disability coverage
• Annual learning and development stipend
• Daily meals in offices, and meal delivery credits as eligible
• Relocation support for eligible employees
• Additional taxable fringe benefits (e.g., charitable donation matching, wellness stipends)