ChatGPT Mil Enablement Lead

Location: Hybrid - Reston, VA, United States; EST required

Employment: 1099 Contract Employment

About the Team

The Carahsoft's ChatGPT Mil enablement team helps Department of War (DoW) organizations turn access to AI into confident, responsible, mission-relevant use. The team works with customer leaders, program owners, technical practitioners, and front-line personnel to build practical skills and support adoption across varied missions and operating environments.

Our work combines live facilitation, instructional design, customer advisory, adoption support, and reusable learning resources. We partner with Technical Success, Customer Success, Solutions, Product, and other internal teams to align enablement with customer priorities and confirmed ChatGPT Mil capabilities.

This role will support the larger ChatGPT Mil motion but also be assigned to be the lead enabler of a particular Force (Army, Navy, Air Force, Space Force, Marines, etc). Daily activities may range from a single executive session to a multi-session launch, workshop series, or adoption program.

About the Role

You will prepare and lead strategic training plans with the customer, partners and key entities like CDAO. You will design and create content to lead virtual and onsite learning experiences for audiences with different roles, missions, technical backgrounds, and levels of AI experience. The work may include introductory ChatGPT Mil sessions, advanced workshops, executive concierge support, role-based learning, and Codex training for technical practitioners.

This role requires strong facilitation, practical product fluency, sound instructional judgment, and the ability to adapt in real time. You will translate technical concepts into clear instruction, help customers apply AI to realistic government workflows, and convert lessons from individual engagements into materials that can be reused across programs.

Overall Responsibilities:

• Lead virtual and onsite ChatGPT Mil training for senior leaders, program owners, technical teams, operational personnel, and other customer audiences.
• Host solutions workshops, onboarding sessions, advanced capability sessions, and other customer learning engagements.
• Conduct high-touch, one-on-one concierge sessions that help senior leaders understand practical uses, limitations, responsible-use considerations, and organizational adoption needs.
• Lead Codex training for technical practitioners and other audiences learning to use AI-supported development workflows.
• Design training material including but not limited to prompt packs, quick start guides, training videos and deployment guides that are grounded in realistic tasks, decisions, documents, and collaboration patterns.
• Adapt session content, pacing, examples, and delivery methods to each customer's mission, priorities, constraints, and level of AI experience.
• Prepare clear demonstrations and hands-on exercises using approved or synthetic material appropriate to the customer environment.
• Answer questions, troubleshoot issues, and adjust instruction during live sessions while maintaining accuracy and learning objectives.
• Travel to customer sites as needed to support launches, workshops, executive engagements, and sustained adoption programs.
• Partner with internal teams to coordinate customer engagements and address recurring needs.
• Gather participant feedback and adoption signals, identify patterns, and turn those lessons into improved programs and reusable resources.
• Keep all materials accurate, current, accessible, and aligned with confirmed ChatGPT Mil capabilities, customer handling requirements, and responsible-use practices.

Required Qualifications:

• Have experience delivering customer-facing training, enablement, education, adoption, or transformation programs.
• Are a clear communicator who can engage audiences with varied responsibilities and technical experience.
• Can work effectively with senior leaders, technical teams, program owners, facilitators, and front-line personnel - preferably highly familiar with the US Military.
• Bring practical fluency with ChatGPT, Codex, prompting, and AI-supported development workflows.
• Can translate technical concepts into accurate, mission-relevant instruction.
• Have worked with government customers or similarly complex, regulated organizations with significant privacy, security, and operational constraints.
• Can manage multiple engagements, prepare efficiently, and adapt when customer needs or live-session conditions change.
• Exercise sound judgment when handling privacy, security, product limitations, and responsible AI use.
• Are willing and able to travel to customer sites as engagement needs require.
• Have worked with DoW in the past.
• Have in-depth knowledge of the US Military and ideally have served
• Maintain positive relationships with those still serving
• Understand the command and control of the Military, and is familiar with the military culture, norms, etc.
• Must possess, or be able to obtain and maintain, a favorable High-Risk Public Trust (Tier 4) determination or a Top Secret security clearance, as required by the government customer.

Location and Travel

This is a hybrid role based around Reston, VA. Eligible work locations and any geographic or time-zone requirements are based on customer's needs.

Travel to DoW customer sites is required as needed for training, launches, workshops, executive engagements, and adoption programs.

Compensation and Benefits

• Starting compensation range: $15,000 - $20,000 per month

Carahsoft is an equal opportunity company. Qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, sexual orientation, gender identity, disability, or protected veteran status.

In compliance with the ADA Amendments Act (ADAAA), if you have a disability and would like to request an accommodation in order to apply for a position with Carahsoft, please call 703-230-7487 or e-mail Jessica.Smith@carahsoft.com.

Apply for the Position

First Name Required

Last name Required

Phone Required

Email Required

Upload Resume Required

Notes