Training and Enablement Specialist

About Cadre AI

Cadre AI is an AI strategy and integration firm that partners deeply with organizations to transform workflows, streamline operations, and deliver measurable business outcomes. We operate at the intersection of strategy, engineering, and adoption, ensuring AI delivers real, lasting impact for the B2B companies we serve.

Cadre AI works with clients ranging from private equity portfolio companies to enterprise SaaS teams, and training is how we turn AI adoption into a business result instead of a workshop. You will lead the sessions that make that happen: live, high-stakes training with client teams from the C‑suite to the front line, delivered well enough that clients ask for more of it.

Most weeks split two ways. Some days you are in front of a client delivering a session. Other days you are heads‑down building and refining the training methodology, templates, and product that make the next session better and more repeatable. You thrive here if you like being in the room with executives, can translate technical AI concepts into plain language on the fly, and get real satisfaction from building a repeatable system instead of reinventing every deck.

You will report to Cadre's VP of Learning & Enablement and be part of the team that builds the reusable assets and libraries that come out of the sessions you deliver. As Cadre's training practice grows into a standalone product line, you will be one of the people building what that product actually is, not just running someone else's material.

• 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.

• 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), or the instinct to seek them out, since content that does not change behavior on the job does not count as a win here.
• 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…