AI Transformation Lead/Strategist

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 Transformation Lead / Strategist, you'll work directly with executive teams and their organizations to guide them through the most significant technological shift of our generation. You'll have the autonomy to define how we serve clients, the visibility to establish yourself as a leader in this space, and the impact of transforming how companies adopt AI.
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

• Deep understanding of organizational change management - you know that AI transformation is about people and culture, not just AI tools

• Proven ability to build relationships and credibility with senior executives and stakeholders

• Strong business acumen and the ability to connect AI capabilities to tangible business outcomes

• Exceptional communication skills - you can make complex ideas accessible and compelling to diverse audiences

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

• Track record of delivering measurable results in client-facing roles

• Natural coaching ability and passion for developing others

• 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.