AI Workforce Enablement Lead | People Team (Remote)

About the Role

Progressive Leasing, a leading provider of in-store and e-commerce lease-to-own solutions, is hiring an AI Workforce Enablement Lead to support our enterprise AI transformation. This remote position can be performed anywhere in the continental US. As part of PROG Holdings, a FinTech holding company, we value inclusive collaboration, innovation, and development.

Who We Are

The People team at PROG is lean, deeply embedded with the business, and at the center of our shift. We partner across Talent, HR, and Technology to redesign work thoughtfully and move our workforce forward with clarity and confidence.

Who You Are

A workforce enablement and change-execution advisor with experience turning transformation goals into real behavior change. You operate well in ambiguity, partner naturally with the business, and own outcomes end-to-end. You focus on functionality and practical solutions that drive adoption.

Responsibilities

• Shape and guide the workforce enablement approach for AI-driven workflow and role changes
• Design and run enablement programs that drive genuine adoption
• Equip managers to lead their teams through transition, including readiness, support, and challenging conversations
• Translate redesigned workflows into clear role expectations, skills, and enablement plans
• Build practical toolkits, learning experiences, and manager resources
• Advise across Talent, HR, and AI teams to ensure enablement precedes accountability shifts
• Measure progress with leading indicators like behavior change and readiness
• Continuously refine the approach based on employee and manager feedback

Qualifications

• 5+ years in workforce transformation, people enablement, or talent-side change execution
• Track record of driving real behavior change, not just delivering training or communications
• Fluency with HR/Talent systems (role design, skills, learning, performance)
• Strong judgment, autonomy, and follow-through in fast-paced environments
• Ability to diagnose resistance and tailor support
• Practical experience with AI-enabled ways of working
• Instinct for building functional, adoptable solutions

About Us

Progressive Leasing welcomes diversity and does not discriminate in any aspect of employment. We are an equal opportunity employer committed to creating an inclusive environment.