Why This Job is Featured on The SaaS Jobs
AI deployment in SaaS increasingly hinges on proving value quickly inside complex enterprise environments, and this role sits directly in that problem space. By owning structured pilots for products like ChatGPT Enterprise and Codex, the work focuses on turning early experimentation into evidence that decision makers can act on, a core motion for modern AI software sold on subscription and expansion.
For a SaaS career, the standout theme is building repeatable adoption and evaluation mechanics. Running 30 to 45 day pilots forces disciplined scoping, measurement, and stakeholder alignment, while also requiring enough technical fluency to navigate data access, security constraints, and workflow integration. The emphasis on capturing patterns and turning them into playbooks is particularly transferable across SaaS organizations that rely on consistent pre and post sales execution to scale.
This position fits professionals who enjoy operating at the intersection of customer outcomes and product capability, and who are comfortable presenting clear recommendations to executive audiences. It also suits operators who prefer ambiguity with structure, using tight timelines, defined success criteria, and cross functional coordination to keep multi stakeholder initiatives moving.
The section above is editorial commentary from The SaaS Jobs, provided to help SaaS professionals understand the role in a broader industry context.
Job Description
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.
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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