AI Trainer & Educator

Pragmatico helps companies transform the culture around AI so that its use becomes a daily habit, enabling them to achieve productivity gains quickly. We're a values-driven company led by exited founders, already cash-flow positive and well-capitalized. This is your chance to get in on the ground floor to shape how we deliver transformation, grow alongside a rapidly scaling company, and help organizations fundamentally reimagine how they work.

As an AI Trainer & Educator, you'll be on the front lines of transformation, teaching everyone from executives to individual contributors how to use AI in their daily work. You'll stay current on AI developments and translate them into compelling, practical training that builds confidence and capability. This role combines technical AI fluency with engaging presentation skills. As we scale, you could lead a training team that multiplies your impact across clients.

Our approach to hiring: We're more interested in capability and fit than titles. These roles can be filled at junior, mid, or senior levels depending on your experience. We're ready to bring on full-time founding team members now - though for the right person in the right situation, part-time starts with a clear path to full-time is possible.

Responsibilities

• Lead end-to-end client transformations through Pragmatico's 3-phase adoption system, from initial leadership alignment through organization-wide rollout and sustained adoption

• Serve as the strategic quarterback for complex, multi-month client engagements - you're part consultant, part coach, part project quarterback, combining strategy with hands-on delivery

• Build trusted advisor relationships with client leadership teams, understanding their business challenges and translating them into actionable AI transformation strategies

• Adapt and evolve our methodology based on client needs and emerging best practices, contributing to the continuous improvement of our approach

• Guide change management efforts that address the human side of AI adoption, including building psychological safety, overcoming resistance, and creating sustainable behavioral change

• Collaborate cross-functionally with trainers, project managers, and leadership to ensure seamless client experiences

• Monitor client engagement progress against established KPIs and milestones, providing regular reporting to internal leadership and client stakeholders

• For senior-level hires: Mentor and develop junior transformation leads as the team scales. Direct path to leadership as we add more transformation leads.

Qualifications

• Hands-on fluency with AI tools and a deep understanding of their practical applications across business functions

• Exceptional presentation and facilitation skills with the ability to make technical concepts accessible and engaging

• Experience designing or delivering training, workshops, or educational programs to diverse audiences

• Natural ability to build rapport and create psychological safety so learners feel comfortable experimenting and asking questions

• Intellectual curiosity and commitment to continuous learning in a rapidly evolving field

• Strong communication skills with the ability to adjust your approach based on audience needs and learning styles

• Comfort with ambiguity and the flexibility to adapt content and delivery on the fly

• Entrepreneurial mindset with the adaptability to thrive in a fast-moving startup environment

About Pragmatico

Pragmatico transforms mid-market companies into AI-native to win in the AI economy. Founded by exited, operational business leaders, the firm guides companies through every stage of AI transformation: AI vision, policy, psychological safety, training/upskilling, and adoption and ROI analytics. Pragmatico's mission is to make AI adoption human, practical, and permanent. Learn more at www.pragmatico.ai.

Equal Opportunity Statement

Pragmatico is an equal opportunity employer, and all qualified applicants will receive consideration for employment without regard to gender, age, race, religion, or any other classification that is protected by applicable law.