AI Documentation Specialist (Senior)

DecisionPoint | Cortek • Chicago, IL

11d • Remote

About The Position

DecisionPoint seeks a Senior AI Documentation Specialist to create and maintain technical documentation supporting the integration of artificial intelligence into USMEPCOM workflows and operations under the ENLIST program. The role works with the AI Integration Lead and technical teams to document AI-enabled workflows, secure data pipelines, model-monitoring processes, and automated multi-step agents. The specialist translates technical information into implementation documentation, operating procedures, maintenance guidance, and user instructions.

The specialist supports consistent documentation throughout implementation, workforce adoption, releases, and ongoing operations, helping technical personnel maintain AI capabilities and users operate them within approved workflows. The position is remote, with Chicago-area candidates preferred. Applicants acknowledge and consent to their resumes being included in an active competitive government contract bid.

Requirements

• Active Secret clearance or higher.
• Minimum of eight years of relevant professional experience.
• Bachelor’s degree in technical communication, English, information systems, or a related field, or a permitted equivalent.
• Experience documenting AI workflows.
• Experience documenting data pipelines.
• Experience documenting model-monitoring processes.
• Experience developing operating procedures and user guidance.
• Ability to create and maintain technical documentation supporting AI implementation, workforce use, and ongoing maintenance.
• Ability to collaborate with the AI Integration Lead and technical teams to document AI-enabled workflows, secure data pipelines, and automated multi-step agents.

Nice To Haves

• Relevant AI or cloud fundamentals certification.
• Documentation-tool training.
• Experience supporting federal or Department of Defense technical documentation.
• Experience documenting knowledge assistants, retrieval workflows, AI agents, or machine learning operations.
• Familiarity with cloud platforms, APIs, authentication, access controls, audit logging, and automated testing.
• Experience documenting human approval checkpoints, exception handling, troubleshooting, and recovery procedures.
• Experience with SharePoint, Confluence, Markdown, version-controlled documentation, or comparable publishing platforms.
• Experience developing accessible documentation, process diagrams, knowledge articles, and task-based user guides.
• Familiarity with document review, approval, configuration management, and release processes.
• Strong technical interviewing, editing, organization, and stakeholder communication skills.

Responsibilities

• Create and maintain technical documentation for AI integration within USMEPCOM processes and operations.
• Gather and validate technical information with the AI Integration Lead, engineers, developers, data professionals, cybersecurity personnel, and mission representatives.
• Document AI-enabled workflows, including inputs, outputs, dependencies, decision points, user actions, and exception paths.
• Develop workflow diagrams, process descriptions, implementation guides, operating procedures, and maintenance instructions.
• Document secure data pipelines, including data sources, transformations, interfaces, access requirements, dependencies, and operational checks.
• Maintain documentation for model-monitoring processes, performance measures, drift indicators, alert thresholds, escalation paths, and corrective actions.
• Document automated multi-step agents, including task sequences, available tools, permissions, operating boundaries, approval checkpoints, and failure handling.
• Prepare user guidance on intended uses, expected behavior, limitations, source references, human-review requirements, and escalation procedures.
• Document installation, configuration, deployment, rollback, troubleshooting, and recovery procedures using technical-team inputs.
• Maintain descriptions of relevant APIs, application interfaces, data flows, and integration dependencies.
• Coordinate technical reviews to confirm documentation accurately reflects approved designs and implemented functionality.
• Update documentation following releases, configuration changes, workflow revisions, incidents, and lessons learned.
• Maintain document versions, revision histories, review records, approval status, and publication schedules.
• Organize documentation repositories so users and technical teams can locate current, approved information.
• Apply consistent terminology, templates, formatting, and cross-references across documentation products.
• Coordinate with workforce enablement and training personnel to align user guides, job aids, exercises, and technical references.
• Support implementation reviews, operational handoffs, knowledge transfer, and documentation readiness assessments.
• Track documentation gaps, review comments, outstanding decisions, and corrective actions through completion.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior