AHEAD

digital business

TechnicalTrainer,AI&Enablement

$102–135k Chicago, Illinois, United States FULL TIME Remote Friendly
Market Sentiment
HIGH DEMAND

Neural analysis suggests this role is
optimal for Mid candidates.

The Brief

“Technical Trainer, AI & Enablement at AHEAD. Skills: AI Training, LLM Enablement, Prompt Engineering, Technical Facilitation. Design and deliver AI training. Build and maintain learning paths”

Industry & Context.

digital business
Problems you'll solve

Debug prompts; Debug workflows; Explore edge cases; Understand limitations; Understand risks

What They're Looking For.

Must Have

5–8 years of relevant experience in one or more of: AI/ML, data/analytics, or software engineering roles with an 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, 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, judgment, and comfort operating in fast-moving, ambiguous environments

What You'll Do.

Design and deliver AI training

Build and maintain learning paths

Test AI tools and workflows

Partner to turn AI ideas into use cases

Maintain awareness of AI training

Create social learning spaces

Gather feedback and improve content

How You'll Work.

Team & Collaboration

Work closely with AI Strategy Team; Partner with eTech; Collaborate with Talent Development; Work with technical leaders; Work with business leaders; Work across technical stakeholders; Work across non-technical stakeholders; Work across multiple teams; Work across functions

Communication Scope

Excellent communication; Translate complex technical concepts; Explain complex technical ideas

Full Job Description

## Description AHEAD builds platforms for digital business. By weaving together advances in cloud infrastructure, automation and analytics, and software delivery, we help enterprises deliver on the promise of digital transformation.   At AHEAD, we prioritize creating a culture of belonging, where all perspectives and voices are represented, valued, respected, and heard. We create spaces to empower everyone to speak up, make change, and drive the culture at AHEAD.    We are an equal opportunity employer, and do not discriminate based on an individual's race, national origin, color, gender, gender identity, gender expression, sexual orientation, religion, age, disability, marital status, or any other protected characteristic under applicable law, whether actual or perceived.    We embrace all candidates that will contribute to the diversification and enrichment of ideas and perspectives 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. ## Duties/Reponsibilities 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.

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