Training and Enablement Specialist
About The Position
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 involves leading high-stakes training sessions with client teams, from C-suite to front line, to turn AI adoption into business results. The position requires a blend of client-facing delivery and back-end development of training methodology, templates, and products. The ideal candidate thrives in client-facing executive interactions, can translate technical AI concepts into plain language, and enjoys building repeatable systems. The role reports to Cadre's VP of Learning & Enablement and will contribute to building the company's training practice into a standalone product line.
Requirements
- 3-5+ years designing and delivering corporate training or enablement programs.
- Experience facilitating live sessions in front of senior or executive audiences.
- Working knowledge of adult learning and skill transfer principles (e.g., action mapping, Kirkpatrick) or the ability to seek them out.
- Experience contributing to or building a training curriculum, workshop series, or certification product.
- Experience with AI tools, specifically Claude, both as a subject matter and a daily tool for prep and content iteration.
- Comfortable using ClickUp or similar project management tools to track multiple concurrent client engagements.
- Strong verbal and written communication skills, with the ability to translate technical or strategic AI concepts for non-technical executives.
- A bias toward building systems and templates over one-off efforts.
- Self-directed and comfortable with ambiguity; ability to help define Cadre's training playbook.
- Based in San Diego with a willingness to travel for in-person facilitation and team collaboration.
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.
- Facilitate hands-on workshops that get participants using AI tools directly.
- Manage the run-of-show for each engagement: pre-session prep, materials, timing, and follow-up.
- Gather insights from live sessions (prompts, questions, sticking points) and integrate them into Cadre's training content.
- Contribute to building Cadre's standalone, sellable training products.
- Help define what a repeatable training offer looks like, including templated and client-specific components.
- Apply adult learning and skill transfer principles to training design to drive behavior change.
- Build and refine templates, run-of-show documents, and delivery playbooks to ensure consistent training quality.
- Identify and address inefficiencies or inconsistencies in Cadre's training processes.
Benefits
- Access to the frontier of AI through partnerships with Anthropic and OpenAI.
- Opportunity to shape Cadre's standalone sellable training offerings.
- AI-native culture with a focus on using AI for internal operations.
- Upside potential in a bootstrapped, profitable, and fast-growing company.
- A culture with clear accountability and where the best idea wins.
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What This Job Offers
Job Type
Full-time
Career Level
Mid Level
Education Level
No Education Listed
