AI Deployment Manager - Pilots - San Francisco

Details

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. The role focuses on helping customers evaluate OpenAI products in real-world contexts, identify high-value use cases, and generate clear, decision-ready signals tied to business value.

The role designs and leads 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 adoption, and translating pilot outcomes into recommendations that support expansion or purchase decisions.

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 high-impact use cases that can generate credible signals 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 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, proofs of concept, 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 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.
• Ability to operate in fast-paced, ambiguous environments, making real-time tradeoffs while maintaining clarity and momentum.
• High ownership mindset and a collaborative approach to driving outcomes across sales, technical, and customer stakeholders.
• Commitment to the responsible and ethical deployment of AI.

Benefits

• Base salary of $162,000–$230,000 per year, plus equity.
• Medical, dental, and vision insurance, with employer contributions to Health Savings Accounts.
• Pre-tax Flexible Spending Accounts, dependent care, and commuter benefits.
• 401(k) retirement plan with employer match.
• Paid parental, medical, and caregiver leave.
• Paid time off, company holidays, and paid office closures.
• Mental health and wellness support.
• Employer-paid basic life and disability coverage.
• Annual learning and development stipend.
• Office meals and eligible meal delivery credits.
• Relocation support for eligible employees.
• Additional benefits may include charitable donation matching and wellness stipends.