AI Training Lead: Exec Sessions & Enablement Products

Cadre AI; San Diego, Northern (CA, KY); Hybrid; USD 90,000 - 140,000; Full time

Job summary

Cadre AI is seeking a seasoned Training & Enablement professional to lead live AI training sessions for executive and front-line teams, translating complex concepts into actionable workflows. You will also help build reusable training assets and a scalable product line as Cadre's practice grows.

Based in San Diego, you’ll travel as needed to deliver in-person sessions, partner with the VP of Learning & Enablement, and shape templates, playbooks, and curricula that scale beyond one engagement.

Qualifications

• 3-5+ years designing and delivering corporate training or enablement programs, with real experience facilitating live sessions in front of senior or executive audiences, not just building self-paced content.
• Working knowledge of adult learning and skill transfer principles (action mapping, Kirkpatrick, or similar).
• Experience contributing to or building a training curriculum, workshop series, or certification product, not just delivering someone else's material.
• Experience with AI tools, Claude specifically, both as the subject you teach and as a tool you use daily to prep sessions, build assets, and iterate on content.
• Comfortable with ClickUp or similar project tools to track a delivery pipeline across several concurrent client engagements.

Responsibilities

• Lead live AI training sessions for client teams ranging from executive leadership to front-line staff, adapting delivery style and depth to the audience in the room.
• Facilitate hands-on workshops that get participants using AI tools directly, not just watching a demo, since adoption is measured by what people do after the session, not how it felt.
• Manage the run-of-show for each engagement: pre-session prep, materials, timing, and follow-up, so sessions land on schedule and on message.
• Gather what happens in the room, prompts, questions, sticking points, and route it back into Cadre's training content so future sessions get sharper.
• Contribute to building Cadre's standalone, sellable training products, not just custom one-off engagements for a single client.
• Help define what a repeatable training offer looks like: what is templated, what is client-specific, and what can be sold at a set price.
• Bring what you learn from live delivery back into the product so it keeps improving instead of going stale.
• Apply adult learning and skill transfer principles to how Cadre designs training, so sessions are built to change behavior, not just deliver content.
• Build and refine templates, run-of-show docs, and delivery playbooks so training quality does not depend on any one person being in the room.
• Identify where Cadre's training process is slow, or inconsistent, and fix it.

Skills

Corporate training design

Executive training facilitation

AI training with Claude

ClickUp

Verbal & written communication

Tools

Claude AI

Job description

Cadre AI is seeking a seasoned Training & Enablement professional to lead live AI training sessions for executive and front-line teams, translating complex concepts into actionable workflows. You will also help build reusable training assets and a scalable product line as Cadre's practice grows.

Based in San Diego, you’ll travel as needed to deliver in-person sessions, partner with the VP of Learning & Enablement, and shape templates, playbooks, and curricula that scale beyond one engagement.