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.

The Role

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.

What You'll Do

Client Training Delivery

• 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.

Training Product Development

• 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.

Training Design & Process Improvement

• 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.

What You Need to Succeed

• 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 assets, and iterate on content.
• Comfortable with ClickUp or similar project tools to track a delivery pipeline across several concurrent client engagements without dropping a ball.
• Strong verbal and written communication, with the ability to translate a technical or strategic AI concept for a non‑technical executive without dumbing it down.
• A bias toward building systems and templates over one‑off heroics, since this role is being built to scale past any single person's calendar.
• Self‑directed and comfortable with ambiguity: you will help define parts of Cadre's training playbook, not just execute one that already exists.
• Based in San Diego with a willingness to travel since in‑person facilitation and team collaboration are part of the role.

Why Cadre AI

• Build the product, not just deliver it. You will help shape Cadre's standalone sellable training offerings from the inside, not just run sessions someone else designed.
• AI-native culture. We do not just build AI for clients. We use it to run our own operations. You will work with people who are as obsessed with the tools as you are.
• Access to the frontier. Through partnerships with Anthropic and OpenAI, you will be among the first to experiment with new models and capabilities.
• Upside. We are bootstrapped, profitable, and growing fast. Growth means new teams and new initiatives, and room to move into them.
• No bureaucracy. Small, scrappy team. Clear accountability. The best idea wins, regardless of who says it.

If you want a seat where you're in the room with real executives one day and helping build the product the next, this is that seat.