Technical Trainer in Chicago, Illinois at AHEAD

The Technical Trainer, AI & Enablement reports into the Senior Manager, Product Owner, Enterprise Insights & GPT Platform and has a matrix management relationship with the VP, Talent and Workforce Transformation. The trainer helps AHEAD build an AI-powered workforce by turning complex AI tools and concepts into clear, practical training. This role designs and delivers hands-on learning experiences so employees understand how AI tools work, how to use them safely in real workflows, and how to get better results over time. They work closely with the AI Strategy Team, eTech, Talent Development, and technical and business leaders to create AHEAD-specific examples, labs, and resources that go beyond vendor training and support ongoing experimentation and peer learning.

• Design and deliver clear, practical AI training (workshops, labs, demos, and office hours) that show people how our AI tools work and how to use them safely in real work.
• Build and maintain role-based learning paths and reusable prompts, templates, and examples tailored to AHEAD workflows.
• Test AI tools, prompts, and workflows to understand how they behave, where they break, and how guardrails apply before and during rollout.
• Partner with eTech, Talent Development, and the AI Strategy Team to turn AI ideas into concrete use cases, workflows, and training scenarios.
• Maintain enterprise awareness of AI technical training and enablement to ensure all employees know what is available and when.
• Create and support social learning spaces (office hours, communities of practice, internal channels) where employees can share prompts, workflows, and lessons learned.
• Gather feedback, watch how people are using AI, and continuously improve the content, examples, and learning experiences.

• 5–8 years of relevant experience in one or more of: · AI/ML, data/analytics, or software engineering roles with a strong applied AI component, technical enablement, developer relations, or technical training roles
• Demonstrated hands-on experience with LLMs and generative AI, including: designing and testing prompts and workflows, understanding model behavior, limitations, and failure modes
• Strong prompt engineering and experimentation skills, with the ability to articulate “why this works” and “how to debug” prompts and workflows
• Proven facilitation and teaching skills, including the ability to translate complex technical concepts into accessible, actionable content for varied audiences.
• Experience designing and delivering technical enablement (labs, workshops, demos, job aids) rather than purely conceptual training
• Excellent communication and collaboration skills, with comfort working across technical and non-technical stakeholders
• High attention to detail, strong judgment, and comfort operating in fast-moving, ambiguous environments

• Strong practical understanding of LLMs and generative AI, including how to design, test,and debug prompts and workflows.
• Ability to explain complex technical ideas in simple, clear language and turn them into hands-on exercises and examples.
• Skilled facilitator who can lead engaging sessions for both technical and non-technical audiences.
• Comfortable exploring edge cases, limitations, and risks of AI tools and explaining them in a grounded, responsible way.
• Excellent communication and collaboration skills; able to work across multiple teams and functions.
• Organized and detail-oriented, able to manage multiple training offerings and keep content current.
• Thrives in a fast-moving, ambiguous environment; willing to experiment, learn, and iterate based on feedback.