AI Workforce Enablement Lead (Remote)

Progressive Leasing is a leading provider of in-store and e-commerce lease-to-own solutions. With more than 20 years in FinTech, we’ve grown from start-up to industry leader by innovating, simplifying, and valuing people. We are a subsidiary of PROG Holdings (NYSE: PRG), a FinTech holding company with three business segments: Progressive Leasing, Purchasing Power (a leading employee purchase program for consumer products and services using payroll deduction), and Four, a Buy Now Pay Later (BNPL) platform.

Progressive Leasing is a leading provider of in-store and e-commerce lease-to-own solutions. With more than 20 years in FinTech, we’ve grown from start-up to industry leader by innovating, simplifying, and valuing people. We are a subsidiary of PROG Holdings (NYSE: PRG), a FinTech holding company with three business segments: Progressive Leasing, Purchasing Power (a leading employee purchase program for consumer products and services using payroll deduction), and Four, a Buy Now Pay Later (BNPL) platform.

We are currently hiring an AI Workforce Enablement Lead to help support our enterprise AI transformation and ensure our people are set up to succeed as how work gets done evolves.

This role is a work‑from‑home position and can be performed remotely anywhere in the continental US.

Employee Value Proposition (EVP):  PROG is dedicated to providing people with opportunity — opportunity for inclusive collaboration, opportunity for innovation, and opportunity for development.

Who We Are

The People team at PROG is lean, deeply embedded with the business, and operating right at the center of this shift. We partner closely across Talent, HR, and Technology to redesign work thoughtfully and move our workforce forward with clarity and confidence. As a consultant, you'll plug directly into that partnership.
 

Who You Are

A workforce enablement and change-execution advisor who knows how to turn big transformation goals into real, on-the-ground behavior change. You're comfortable operating in ambiguity, you partner naturally with the business, and you own outcomes end-to-end. You think in terms of functionality — will managers actually use this toolkit, will employees actually shift behavior — not just deliverables checked off a list.
 

Scope of the Engagement

• Shape and guide the workforce enablement approach for AI-driven workflow and role changes
• Design and run enablement programs that drive genuine adoption — not "check-the-box" training
• Equip managers to lead their teams through transition, including readiness, support, and the tougher conversations
• Translate redesigned workflows into clear role expectations, skills, and enablement plans
• Build practical, genuinely usable toolkits, learning experiences, and manager resources
• Advise across Talent, HR, and AI teams to ensure enablement lands before accountability shifts
• Measure progress with leading indicators — behavior change, readiness, friction — rather than vanity metrics
• Continuously refine the approach based on real signals from employees and managers
   

What You Bring

• 5+ years in workforce transformation, people enablement, or talent-side change execution
• A track record of driving real behavior change — not just delivering training or communications
• Fluency working inside or alongside HR/Talent systems (role design, skills, learning, performance)
• Strong judgment, autonomy, and follow-through in fast-moving environments
• The ability to diagnose resistance and tailor support to fit
• Practical curiosity and hands-on experience with AI-enabled ways of working (no engineering background required)
• An instinct for functionality — building things people will actually adopt and keep using

Progressive Leasing welcomes and encourages diversity in the workplace. We do not discriminate in any aspect of employment on the basis of race, color, religion, national origin, ancestry, gender, sexual orientation, gender identity and/or expression, age, veteran status, disability, or any other characteristic protected by federal, state, or local employment discrimination laws where Progressive Leasing does business.

Progressive Leasing welcomes and encourages diversity in the workplace. We do not discriminate in any aspect of employment on the basis of race, color, religion, national origin, ancestry, gender, sexual orientation, gender identity and/or expression, age, veteran status, disability, or any other characteristic protected by federal, state, or local employment discrimination laws where Progressive Leasing does business.