AI Trainer

Pragmatico

28d • Onsite

About The Position

Mid-market companies are under real pressure to make AI work across their organizations. Most have decided to invest. Many have started. The hard part, the part almost nobody cracks, is getting an entire workforce to stop attending sessions about AI and start reaching for it reflexively, on real work, every day. That gap is harder to close than it looks. Most AI training produces informed employees. People leave knowing more than they came in with, nodding at everything the trainer said, and then opening their laptops the next day exactly the same way they always have. Knowledge and agreement are not adoption. The canyon between hearing a good idea and actually changing a daily habit is where most AI transformation stalls, and most training was never designed to cross it. That is the gap this role fills. You walk into client organizations at whatever stage they are at, start with the leaders, get the C-suite genuinely proficient and bought in before anyone else, and then bring that same credibility and energy to every level that follows. You won't be primarily building curriculum or managing logistics. Pragmatico's delivery team handles the administrative side, and the training content is already built. Your job is to get people across the canyon: walk into any room, meet the audience where they are, and leave with people who will work differently. When it works, the results show up in the numbers: measurable daily active adoption on AI tools and business outcomes that clients can present to their board.

Requirements

• Demonstrated credibility with executive audiences, whether earned through a background in a high-performance professional field or through years of delivering high-stakes training at the senior leadership level.
• Command a room not through credentials or slides but through demonstrated expertise and the ability to make sophisticated audiences feel the session was built specifically for them.
• Use AI tools every day as core infrastructure.
• Have a genuine personal practice that gives you credibility when you tell a client audience that AI changes how you work.
• Speak from experience, not theory.
• Stay obsessively current on AI platform capabilities, feature releases, and best practices across the full ecosystem.
• Absorb new client contexts fast, knowing enough about the business, the audience, and the pressure points to make every example feel native to their world.
• Hold the room's credibility under pressure, having the precise answer when a skeptic challenges you.
• Know how to find the converted skeptic and give them the floor, rotate who shares so it is never just the stars, and recognize individuals by name so their wins become proof for everyone else.
• Remove friction before you add motivation, looking for what is making AI hard to access and fixing the access before spending energy on persuasion.
• Entrepreneurial mindset with the adaptability to thrive in a fast-moving startup environment.

Responsibilities

• Design every moment around the standard of whether people work differently the next day, not around whether the room is engaged, nodding, or satisfied.
• Show before you tell, every time, getting to the demonstration fast and making it specific to that client's actual work.
• Read the room and sequence to what they are ready for, diagnosing what is actually happening and responding to that, not to the agenda.
• Stay current on platform capabilities, feature releases, and best practices across the full AI ecosystem.
• Surface what is resonating, what is not, and where audiences get stuck, with enough precision to name which principle broke down, at what point, and why.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed