AI Enablement & Training Lead – ChatGPT / Generative AI

Job Title: AI Enablement & Training Lead – ChatGPT / Generative AI

Location: Remote

Position Type: Contract

Mandatory Security Requirement: Candidates must hold an active Top Secret security clearance , as required by the government customer.

Position Overview

We are seeking an experienced AI Enablement & Training Lead to drive ChatGPT Mil adoption, training, and capability development for U.S. government and military customers. This individual will collaborate with customer stakeholders, government leadership, technical teams, and partners, including CDAO, to develop and deliver effective AI training programs.

The ideal candidate will combine strong instructional design and presentation skills with hands-on knowledge of ChatGPT, Codex, prompt engineering, and AI-enabled workflows. The role involves delivering virtual and onsite training, executive-level coaching, technical workshops, and customized learning experiences tailored to military and government environments.

Key Responsibilities

• Develop and execute AI training and enablement strategies in collaboration with government customers, partners, and senior stakeholders.
• Deliver virtual and onsite ChatGPT Mil training to military personnel, senior executives, program managers, technical teams, and operational staff.
• Facilitate introductory sessions, advanced workshops, product demonstrations, onboarding programs, and role-specific training.
• Provide personalized coaching and executive concierge support to help senior leaders understand AI capabilities, limitations, adoption opportunities, and responsible-use practices.
• Conduct Codex training and workshops focused on AI-assisted software development and technical workflows.
• Create and maintain training resources, including prompt libraries, quick-start guides, instructional videos, deployment documentation, and hands-on exercises.
• Customize training content according to mission objectives, audience expertise, operational requirements, and government security policies.
• Demonstrate practical applications of AI using approved or synthetic materials relevant to government and military use cases.
• Address participant questions, resolve training-related issues, and adjust delivery approaches to improve engagement and learning outcomes.
• Travel to customer locations when required for training launches, executive briefings, workshops, and adoption initiatives.
• Collaborate with internal product, technical, and customer success teams to support implementation and adoption.
• Collect participant feedback, evaluate training effectiveness, and continuously improve enablement programs.
• Ensure all training materials remain accurate, accessible, up to date, and aligned with approved product capabilities and responsible AI practices.

Required Qualifications

• Proven experience in customer-facing training, AI enablement, learning and development, technology adoption, or organizational transformation.
• Strong presentation, facilitation, communication, and instructional design skills.
• Hands-on familiarity with ChatGPT, ChatGPT Mil, Codex, prompt engineering, and AI-assisted workflows.
• Ability to translate complex technical concepts into clear, practical, mission-focused training.
• Experience working with U.S. government, Department of Defense (DoD), military, or similarly regulated organizations.
• Strong understanding of U.S. military culture, organizational structure, command-and-control processes, terminology, and operational environments.
• Prior military service or substantial experience supporting U.S. military personnel and leadership is highly desirable.
• Established professional relationships with military or government stakeholders are a plus.
• Ability to engage effectively with senior executives, military leaders, technical practitioners, program owners, and frontline personnel.
• Experience managing multiple training engagements, adapting to changing requirements, and delivering effective sessions in dynamic environments.
• Strong judgment regarding data privacy, information security, responsible AI use, and technology limitations.
• Willingness and ability to travel to customer sites as required.
• Must possess an active, favorable High-Risk Public Trust (Tier 4) determination or an active Top Secret security clearance , as required by the government customer.